UNITED STATES
                       SECURITIES AND EXCHANGE COMMISSION
                             Washington, D.C. 20549

                                   FORM N-CSR

              CERTIFIED SHAREHOLDER REPORT OF REGISTERED MANAGEMENT
                              INVESTMENT COMPANIES

                  Investment Company Act file number 811-21681
                                                     ---------

                       Old Mutual/Claymore Long-Short Fund
                       -----------------------------------
               (Exact name of registrant as specified in charter)

                   2455 Corporate West Drive, Lisle, IL 60532
                   ------------------------------------------
               (Address of principal executive offices) (Zip code)

                                J. Thomas Futrell
                   2455 Corporate West Drive, Lisle, IL 60532
                   ------------------------------------------
                     (Name and address of agent for service)

       Registrant's telephone number, including area code: (630) 505-3700
                                                           ----------------

                      Date of fiscal year end: December 31
                                              ------------

                     Date of reporting period: June 30, 2009
                                               -------------

Form N-CSR is to be used by management investment companies to file reports with
the Commission not later than 10 days after the transmission to stockholders of
any report that is required to be transmitted to stockholders under Rule 30e-1
under the Investment Company Act of 1940 (17 CFR 270.30e-1). The Commission may
use the information provided on Form N-CSR in its regulatory, disclosure review,
inspection, and policymaking roles.

A registrant is required to disclose the information specified by Form N-CSR,
and the Commission will make this information public. A registrant is not
required to respond to the collection of information contained in Form N-CSR
unless the Form displays a currently valid Office of Management and Budget
("OMB") control number. Please direct comments concerning the accuracy of the
information collection burden estimate and any suggestions for reducing the
burden to Secretary, Securities and Exchange Commission, 450 Fifth Street, NW,
Washington, DC 20549-0609. The OMB has reviewed this collection of information
under the clearance requirements of 44 U.S.C. Section 3507.



ITEM 1.  REPORTS TO STOCKHOLDERS.

The registrant's semi-annual report transmitted to shareholders pursuant to Rule
30e-1 under the Investment Company Act of 1940, as amended (the "Investment
Company Act"), is as follows:



   SEMIANNUAL
       REPORT                          OLD MUTUAL/CLAYMORE LONG-SHORT FUND | OLA
June 30, 2009
  (Unaudited)



                            Picture of boats sailing



Logo OLD MUTUAL | Asset                                        Logo CLAYMORE(SM)
                | Management



                                                            WWW.CLAYMORE.COM/OLA


                                                   ...your course to the LATEST,
                                           most up-to-date INFORMATION about the
                                             Old Mutual/Claymore Long-Short Fund

Graphic:
                           OLA    | Old Mutual/
                          LISTED  | Claymore
                          NYSE(R) | Long-Short Fund

Logo OLD MUTUAL | Asset                                        Logo CLAYMORE(SM)
                | Management

    There can be no assurance the Fund will achieve its investment objective.
      The value of the Fund will fluctuate with the value of the underlying
     secutities. Historically, closed-end funds often trade at a discount to
                             their net asset value.

           NOT FDIC-INSURED    NOT BANK GUARANTEED    MAY LOSE VALUE


The shareholder report you are reading right now is just the beginning of the
story. Online at WWW.CLAYMORE.COM/OLA, you will find:

o    Daily, weekly and monthly data on share prices, distributions and more

o    Portfolio overviews and performance analyses

o    Announcements, press releases and special notices

o    Fund and adviser contact information

Analytic Investors, LLC and Claymore are continually updating and expanding
shareholder information services on the Fund's website, in an ongoing effort to
provide you with the most current information about how your Fund's assets are
managed, and the results of our efforts. It is just one more way we are working
to keep you better informed about your investment in the Fund.


2 | Semiannual Report | June 30, 2009



OLA | Old Mutual/Claymore Long-Short Fund

Dear SHAREHOLDER |

We thank you for your investment in the Old Mutual/Claymore Long-Short Fund (the
"Fund"). This report covers the Fund's performance for the semiannual period
ended June 30, 2009.

The Fund's investment objective is to provide a high level of current income and
gains with a secondary objective of long-term capital appreciation. The Fund
seeks to achieve these objectives by investing in a diversified portfolio of
common stocks and other equity securities utilizing a 130/30 long/short strategy
and opportunistically employing a strategy of writing (selling) calls on equity
indices and, to a lesser extent, on individual securities held in the Fund's
portfolio.

During the period covered by this report, Analytic Investor, Inc. ("Analytic"),
the Fund's investment sub-adviser, also pursued a global asset allocation
strategy which sought to generate incremental investment returns with a low
correlation to the rest of the Fund's portfolio by taking long and short
positions in global equity and fixed-income markets. Given the unprecedented
volatility in the market and performance of the global asset allocation, the
Fund announced on July 20, 2009 that it is suspending its use of this component
of its overall investment strategy. The other elements of the strategy remain
unchanged.

Claymore Advisors, LLC ("Claymore") is the Investment Adviser to the Fund.
Claymore entities provided supervision, management, servicing and/or
distribution on approximately $12.9 billion in assets as of June 30, 2009. As
the Fund's investment sub-adviser, Analytic is responsible for day-to-day
management of the Fund's investments. The firm, established in 1970, is an
affiliate of Old Mutual (US) Holdings Inc., more commonly known as Old Mutual
Asset Management. Analytic specializes in the creation and continuous management
of optioned-equity and optioned-debt portfolios for mutual funds, foundations,
insurance companies, endowments, profit-sharing plans, funds of hedge funds, and
individual investors. As of June 30, 2009, Analytic managed or supervised
approximately $8.5 billion in assets.

We believe that the Fund provides shareholders with the potential to outperform
the S&P 500 Index over full market cycles through its multi-strategy approach to
investing. Analytic has employed the Fund's strategy for nearly three decades in
other investment products for institutional and retail investors. While the
Fund's options overlay has similarities to a covered call fund, the Fund's
130/30 long/short equity security selection makes it different. We believe that
this multi-strategy approach provides opportunities unavailable in a traditional
covered call fund.

All Fund returns cited--whether based on net asset value ("NAV") or market
price--assume the reinvestment of all distributions. For the six months ended
June 30, 2009, the Fund provided a total return based on market price of 4.25%
and a total return based on NAV of -2.20%. As of June 30, 2009, the Fund's
market price of $7.66 per share represented a discount of 18.07% to its NAV of
$9.35 per share. Past performance is not a guarantee of future results.

The market value of the Fund's shares fluctuates from time to time, and it may
be higher or lower than the Fund's NAV. The current discount to NAV may provide
an opportunity for suitable investors to purchase shares of the Fund below the
market value of the securities in the underlying portfolio. We believe that,
over the long term, the progress of the NAV will be reflected in the market
price return to shareholders.

The Fund paid quarterly dividends of $0.40 on March 31, 2009, and $0.24 on June
30, 2009. The most recent dividend represents an annualized distribution rate of
12.5% based on the Fund's closing market price of $7.66 on June 30, 2009. Each
of the distributions was accompanied by a letter detailing the expected
characterization of the distribution for federal income tax purposes. These
letters are also posted on the Fund's website. There is no guarantee that the
current level of income will be maintained.

                                           Semiannual Report | June 30, 2009 | 3



OLA | Old Mutual/Claymore Long-Short Fund | DEAR SHAREHOLDER continued


We encourage shareholders to consider the opportunity to reinvest their
distributions from the Fund through the Dividend Reinvestment Plan ("DRIP"),
which is described in detail on page 27 of the Fund's semiannual report. When
shares trade at a discount to NAV, the DRIP takes advantage of the discount by
reinvesting the quarterly dividend distribution in common shares of the Fund
purchased in the market at a price less than NAV. Conversely, when the market
price of the Fund's common shares is at a premium above NAV, the DRIP reinvests
participants' dividends in newly-issued common shares at NAV, subject to an IRS
limitation that the purchase price cannot be more than 5% below the market price
per share. The DRIP provides a cost-effective means to accumulate additional
shares and enjoy the benefits of compounding returns over time. Since the Fund
endeavors to maintain a steady quarterly distribution rate, the DRIP plan
effectively provides an income averaging technique, which causes shareholders to
accumulate a larger number of Fund shares when the market price is depressed
than when the price is higher.

To learn more about the Fund's performance and investment strategy, we encourage
you to read the Questions & Answers section of the report, which begins on page
5. You will find information about Analytic's investment philosophy and
discipline, its views on the market environment and how it structured the Fund's
portfolio based on its views.

We appreciate your investment and look forward to serving your investment needs
in the future. For the most up-to-date information on your investment, please
visit the Fund's website at www.claymore.com/ola.

Sincerely,

/S/ J. Thomas Futrell

J. Thomas Futrell
Chief Executive Officer
Old Mutual/Claymore Long-Short Fund

AN UPDATE ON THE FUND

AGREEMENT AND PLAN OF MERGER

On July 17, 2009, Claymore Group Inc., the parent of the Investment Adviser,
entered into an Agreement and Plan of Merger between and among Claymore Group
Inc., Claymore Holdings, LLC and GuggClay Acquisition, Inc., (with the latter
two entities being wholly-owned, indirect subsidiaries of Guggenheim Partners,
LLC ("Guggenheim")) whereby GuggClay Acquisition, Inc. will merge into Claymore
Group Inc. which will be the surviving entity. The parties intend that the
completed merger will result in a change-of-control whereby Claymore Group Inc.
and its subsidiaries, including the Investment Adviser, will become indirect,
wholly-owned subsidiaries of Guggenheim. The transaction is not expected to
affect the daily operations of the Fund or the investment management activities
of the Investment Adviser.

Under the 1940 Act, consummation of this transaction will result in the
automatic termination of the Advisory Agreement. Accordingly, prior to such
consummation, the Fund expects to enter into a new investment advisory agreement
with the Investment Adviser, to become effective upon the consummation of the
transaction. This new investment advisory agreement will be subject to the
initial approval of the Board of Trustees and subsequent approval by the Fund's
shareholders.

4 | Semiannual Report | June 30, 2009


OLA | Old Mutual/Claymore Long-Short Fund

QUESTIONS & ANSWERS |

DENNIS M. BEIN, CFA
CHIEF INVESTMENT OFFICER, PORTFOLIO MANAGER
ANALYTIC INVESTORS, LLC ("ANALYTIC")
As Chief Investment Officer, Dennis Bein oversees the implementation of
Analytic's investment strategies. He is a major contributor to Analytic's
ongoing research efforts as well as to the new product development efforts and
strategy applications. As Portfolio Manager, Bein directs the Old
Mutual/Claymore Long-Short Fund's (the "Fund's") management team on day-to-day
portfolio management and research related to the Fund's equity-based investment
strategies. Bein joined Analytic in 1995 and has worked as an investment
professional since 1990. He is a CFA charterholder and earned an M.B.A. from the
Anderson Graduate School of Management at the University of California,
Riverside.

The Fund is managed by Analytic Investors, LLC. In the following interview,
Chief Investment Officer and Portfolio Manager Dennis Bein, CFA, explains the
factors that impacted the Fund's performance for the semiannual period ended
June 30, 2009.


================================================================================
BEFORE DISCUSSING PERFORMANCE, PLEASE DESCRIBE THE FUND'S INVESTMENT OBJECTIVE
AND EXPLAIN HOW ANALYTIC'S INVESTMENT STRATEGY SEEKS TO ACHIEVE IT.

The Fund's primary investment objective is to provide a high level of current
income and gains, with a secondary objective of long-term capital appreciation.
The Fund seeks to achieve these objectives by investing in a diversified
portfolio of common stocks and other equity securities. Analytic utilizes
quantitative techniques to develop an equity portfolio for the Fund with a level
of diversification and risk similar to that of the S&P 500 Index, but which
attempts to outperform the S&P 500 Index over full market cycles through
individual security selection and other techniques. In addition to purchasing
equity securities (i.e., taking long positions), Analytic attempts to identify
stocks in the S&P 500 Index that it believes will underperform relative to the
average stock in the universe and will sell the securities short on behalf of
the Fund. Alternatively, Analytic may underweight these securities relative to
the weights of securities in the S&P 500 Index.

The Fund intends to pursue a 130/30 strategy, meaning that it intends to take
long equity positions equal to approximately 130% of the Fund's net assets and
short equity positions of approximately 30% of net assets, although the Fund's
long/short exposure is expected to vary over time based on Analytic's assessment
of market conditions and other factors. The Fund will also opportunistically
employ a strategy of writing (selling) call options on equity indices and, to a
lesser extent, individual securities held in the Fund's portfolio. The Fund
intends to write call options representing approximately 80% to 90% of its net
assets, although the extent of the Fund's use of written call options is
expected to vary over time based on Analytic's assessment of market conditions
and other factors (such that it may range from 0% to 100% of net assets). To the
extent used, the option strategy is designed to generate gains from option
premiums in an attempt to enhance distributions payable to the Fund's
shareholders and to reduce overall portfolio risk. Analytic utilizes
quantitative models to develop an equity portfolio believed to offer the
potential for capital appreciation over time. The portfolio is constructed with
a level of risk similar to that of the S&P 500, in terms of sector exposure,
ratio of price to book value, capitalization, beta (sensitivity to broad market
moves) and volatility. However, the portfolio is designed with the objective of
outperforming the index over a full market cycle by having its long positions
invested in the stocks that are expected to outperform, while selling short the
stocks expected to underperform the long positions. To generate income and help
reduce volatility, a call option overlay is applied.

During the period covered by this report, Analytic also pursued a global asset
allocation strategy which sought to generate incremental investment returns with
a low correlation to the rest of the Fund's portfolio by taking long and short
positions in global equity volatility and currency markets. Given the
unprecedented volatility in the market and performance of the global asset
allocation, the Fund announced on July 20, 2009 that it is suspending its use of
this component of the overall investment strategy. The other elements of the
strategy remain unchanged.


================================================================================
PLEASE EXPAND ON THE SPECIFICS OF YOUR PROCESS.

There are three components of the strategy that Analytic believes make the Fund
unique among covered call funds.

STOCK SELECTION. Analytic begins by analyzing stock characteristics rather than
focusing on individual stocks as many investment managers do. A quantitative
review is based on sophisticated mathematical models focused on variables that
cover multiple dimensions of a stock's value, such as its valuation, growth
potential, historical return patterns, liquidity and risk. The models identify
characteristics that investors are currently rewarding or punishing by examining
a universe of approximately 3,000 stocks to determine which financial
characteristics are shared by the market's largest gaining or losing stocks.
Stocks possessing favorable characteristics are ranked and become candidates for
the long portfolio. Stocks that possess unfavorable characteristics are
candidates for the short portfolio. Ultimately a portfolio of at least 75
highly-ranked stocks is combined with short positions of at least 20 low-ranked
stocks. Analytic monitors the portfolio on a real-time basis utilizing a
proprietary management system, which identifies media events or changes in
fundamental factors that are potentially significant for the portfolio holdings.
However, securities are traded only when Analytic believes the incremental
return potential will exceed the associated transaction costs.



                                           Semiannual Report | June 30, 2009 | 5


OLA | Old Mutual/Claymore Long-Short Fund | QUESTIONS & ANSWERS continued

OPTIONS OVERLAY. The process used in managing the Fund's option overlay strategy
is unique because Analytic typically does not write (sell) call options on
individual securities held in the Fund's portfolio as a traditional covered call
fund might. Analytic's preference is to sell call options on indices based on
strong convictions about the stocks held in the Fund's portfolio. This strategy
helps preserve the upside potential of the Fund's individual equity holdings,
which is considered to be more important than giving away the upside potential
of the market sectors on which calls have been written. Analytic believes that
giving away market or sector upside potential in exchange for lower overall
volatility and a higher yield provided by the call option premiums benefits the
Fund.


Callout Box:

--------------------------------------------------------------------------------
WHAT IS A SHORT SALE?
A short sale is three-step trading strategy that seeks to capitalize on an
anticipated decline in the price of a security. First, arrangements are made to
borrow shares of the security, typically from a broker. Next, the investor will
sell the borrowed shares immediately in the open market with the intention of
buying them back at some point in the future. Finally, to complete the cycle, at
a later date the investor will repurchase the shares (hopefully at a lower
price) and will return them to the lender. In the end, the investor will receive
the difference if the share price falls, but will of course incur a loss if it
rises.
--------------------------------------------------------------------------------

Callout Box:

--------------------------------------------------------------------------------
WHAT IS AN INDEX OPTION?
An index option is a contract which gives the buyer the right to participate in
market gains over and above (in the case of a call) or below (in the case of a
put) a specified price (the strike price) on or before a pre-determined date
(the expiration date). After this pre-determined date, the option and its
corresponding rights expire. For example, the seller of an index call option is
obligated, until the expiration date, to pay the holder of the option the
difference between the index price and the option's strike price, upon the
holder's request. The price of the option is determined from trading activity in
the options market and generally reflects the relationship between the current
price for the index and the strike price, as well as the time remaining until
the expiration date.
--------------------------------------------------------------------------------


================================================================================
PLEASE PROVIDE AN OVERVIEW OF THE MARKET ENVIRONMENT DURING THE FIRST HALF OF
2009.

Stocks continued to decline through the beginning of the period, but rallied
beginning in March, as investors responded to positive earnings surprises,
Federal Reserve stimulus efforts, and the U.S. Treasury's plan to unload toxic
debt. As the credit markets improved and volatility levels fell, investors
significantly bid up equity prices through the second half of the period. By the
end of the period, however, the rally stalled as investors paused to determine
whether expectations of future economic and profit growth would support a
continued rally. Adding to the uncertainty, economic news was mixed, as
manufacturing appeared to be bottoming and U.S. home sales increased for the
fourth straight month, yet the U.S. jobless rate climbed to 9.5%, its highest
level since 1983.


================================================================================
HOW DID THE FUND PERFORM DURING THE FIRST HALF OF 2009?

All Fund returns cited--whether based on net asset value ("NAV") or market
price--assume the reinvestment of all distributions. For the six months ended
June 30, 2009, the Fund provided a total return based on market price of 4.25%
and a total return based on NAV of -2.20%. As of June 30, 2009, the Fund's
market price of $7.66 per share represented a discount of 18.07% to its NAV of
$9.35 per share. Past performance is not a guarantee of future results.

The market value and NAV of the Fund's shares fluctuate from time to time, and
the Fund's market value may be higher or lower than its NAV. The current
discount to NAV may provide an opportunity for suitable investors to purchase
shares of the Fund below the market value of the securities in the underlying
portfolio. The Investment Adviser believes that, over the long term, the
progress of the NAV will be reflected in the market price return to
shareholders.

The Fund paid quarterly dividends of $0.40 on March 31, 2009, and $0.24 on June
30, 2009. The most recent dividend represents an annualized distribution rate of
12.5% based on the Fund's closing market price of $7.66 on June 30, 2009. Each
of the distributions was accompanied by a letter detailing the expected
characterization of the distribution for federal income tax purposes. (These
letters are also posted on the Fund's website.)


================================================================================
PLEASE EXPLAIN THE CHARACTERISTICS FAVORED BY YOUR QUANTITATIVE MODEL DURING THE
FIRST HALF OF 2009.

Analytic's process is based on the fundamental belief that there is persistency
in the types of stock characteristics investors prefer, and it believes that
portfolios that reflect these biases will add value in the long run. During the
six-month period ended June 30, 2009, an overweight to companies with attractive
asset utilization and predicted earnings to price ratios performed well as
investors continued to reward these characteristics. In addition, underweighting
companies with above average price momentum and high financial leverage
contributed to performance as investors penalized these measures. Overweighting
companies with above average historical earnings to price ratios and growth in
valuation dampened performance as investors turned away from these
characteristics. In addition, underweighting companies with above average
trading volume and growth in market detracted from performance as investors
rewarded these measures.



6 | Semiannual Report | June 30, 2009


OLA | Old Mutual/Claymore Long-Short Fund | QUESTIONS & ANSWERS continued


================================================================================
WHICH DECISIONS REGARDING THE COMMON EQUITY PORTFOLIO HAD THE GREATEST POSITIVE
IMPACT ON PERFORMANCE?

Among the best performing positions this portion of the Fund was a long position
in automobile manufacturer Ford Motor Company (0.2% of total common stocks and
securities sold short). Near the end of the period the automaker announced
several products it will be offering, helping the company to achieve its highest
market share in three years, even as Ford decreased incentive spending in May. A
long position in Corning Incorporated (1.3% of total common stocks and
securities sold short), also contributed, as the specialty glass and ceramics
maker, whose largest business is liquid crystal display sales, announced that it
expected to turn a first-quarter profit, due to an increase in glass orders
early in the period.

Another notable long position adding value to the Fund was Texas Instruments
Inc. (1.2% of total common stocks and securities sold short), a Dallas based
developer/manufacturer of semiconductor and computer technology. Its shares
rallied several times during the period, both following the announcement that it
will expand its microcontroller unit (MCU) portfolio with the acquisition of
Luminary Micro, Inc. (not held in the portfolio at period end), the supplier of
a distinctive type of MCUs, and also after updating its second quarter of 2009
guidance, increasing its expected revenue to $2.3-$2.5billion, compared with the
prior range of $1.95-$2.4 billion.


================================================================================
WHICH AREAS OF THE EQUITY PORTFOLIO HURT PERFORMANCE?

Among the worst performing stocks was a short position in SLM Corporation (0.5%
of total common stocks and securities sold short). The student loan company
announced during the period that the U.S. Department of Education has selected
the company for its Federal Student Aid Title IV Student Loan
Management/Servicing procurement. The contract is for the servicing of federal
student loans owned by the Department of Education. The five-year contract is
expected to begin in mid-to-late August 2009. A short position in
Freeport-McMoRan Copper & Gold, Inc. (not held in the portfolio at period end)
detracted from Fund performance during the period. During the period the
international mining company reported a cash dividend of $1.6875 per share, on
the company's 6(3)/4% mandatory convertible preferred stock. In addition the
company announced a cash dividend of $13.75 per share, on its 5(1)/2%
convertible perpetual preferred stock.

A long position that detracted from Fund performance was Lexmark International,
Inc. (0.3% of total common stocks and securities sold short). Shares in the
printing manufacturer/developer fell on the announcement of sharply falling
first quarter sales as businesses and consumers cut back on purchases of
printers and ink, prompting the company to announce it will close a plant in
Mexico to save money.


================================================================================
WHAT WAS THE IMPACT ON PERFORMANCE OF THE OPTIONS AND GLOBAL ASSET ALLOCATION
PROGRAMS?

Although the net effect of the options program was negative during the six-month
period ended June 30, 2009, as equity markets began to move higher, options
written on the S&P 500 Index early in the period posted positive returns. In
addition, options sold on certain sectors, such as water and utility indices,
contributed to performance, as these sectors underperformed during the period.
Options written on the S&P 100 Index detracted from performance. Also, certain
sector options underperformed, such as call options written on housing and
banking sectors, as these sectors moved higher during the period.

During the six-month period, the global asset allocation strategy generated
minimally positive returns. Positive performance in the in the equity and
currency components were somewhat offset by negative returns in the VIX-CBOE
Volatility Index strategy and tactical asset allocation component. However, this
strategy has been a detractor from performance due to the unprecedented market
volatility. As a result, the Fund has suspended its use of this component of the
investment strategy.

In the equity component, long positions in the Spanish and Swedish markets
outperformed short positions in the French and Japanese markets. Despite global
equity markets finishing up for the period, the tactical asset allocation model
exhibited negative returns on the weakness of the sentiment factor and the
change in volatility factor. In the currency component, long positions in the
Australian Dollar and Japanese Yen outperformed short positions in the Canadian
Dollar and the Euro. Finally, a long position in the VIX negatively impacted
performance as equity markets posted strong gains and volatility moved lower.


================================================================================
WHAT IS THE OUTLOOK FOR THE MONTHS AHEAD, AND HOW IS THE FUND POSITIONED FOR
THAT OUTLOOK?

Despite the recent rally in the equity market, there is considerable uncertainty
regarding the economy and market trends. Since capital markets are highly
sensitive to economic reports, it seems reasonable to expect continued
volatility as the economy begins to show signs of improvement.

Analytic intends to emphasize stocks with attractive historical earnings to
price and cash flow to price ratios. Analytic also intends to focus on select
companies with above average asset utilization, while de-emphasizing companies
with higher-than-average financial leverage. Analytic further anticipates
continuing to seek to emphasize companies with above-average profit margins,
while moving away from companies with high trading volume and above-average
analyst dispersion.

Analytic believes that the Fund's structure and strategy have the potential to
provide attractive returns in a wide variety of market conditions.



                                           Semiannual Report | June 30, 2009 | 7


OLA | Old Mutual/Claymore Long-Short Fund | QUESTIONS & ANSWERS continued


================================================================================
INDEX DEFINITIONS

Indices are unmanaged and it is not possible to invest directly in an index.

The S&P 500 is an unmanaged, capitalization-weighted index of 500 stocks. The
index is designed to measure performance of the broad domestic economy through
changes in the aggregate market value of 500 stocks representing all major
industries.

The S&P 100, a subset of the S&P 500, is comprised of 100 leading U.S. stocks
with exchange-listed options. Constituents of the S&P 100 are selected for
sector balance and represent about 57% of the market capitalization of the S&P
500 and almost 45% of the market capitalization of the U.S. equity markets. The
stocks in the S&P 100 tend to be the largest and most established companies in
the S&P 500.

The VIX-CBOE Volatility Index is widely known as the VIX Index. VIX is the
ticker symbol for the Chicago Board Options Exchange (CBOE) Volatility Index,
which shows the market's expectation of 30-day volatility. It is constructed
using the implied volatilities of a wide range of S&P 500 index options. This
volatility is meant to be forward looking and is calculated from both calls and
puts. The VIX is a widely used measure of market risk and is often referred to
as the "investor fear gauge."


================================================================================
OLA RISKS AND OTHER CONSIDERATIONS

The views expressed in this report reflect those of the portfolio manager only
through the report period as stated on the cover. These views are subject to
change at any time, based on market and other conditions and should not be
construed as a recommendation of any kind. The material may also include forward
looking statements that involve risk and uncertainty, and there is no guarantee
that any predictions will come to pass. There can be no assurance that the Fund
will achieve its investment objectives. The value of the Fund will fluctuate
with the value of the underlying securities. Historically, closed-end funds
often trade at a discount to their net asset value.

As with any stock, the price of the Fund's common shares will fluctuate with
market conditions and other factors. Shares of closed-end management investment
companies frequently trade at a discount from their net asset value. If you sell
your common shares, you may receive more or less than your original investment.
The common shares are designed for long-term investors and should not be treated
as a vehicle for trading.

The Fund will ordinarily have substantial exposure (both long and short) to
common stocks and other equity securities in pursuing its investment objectives
and policies. The market price of common stocks and other equity securities in
which the Fund invests may go up or down, sometimes rapidly or unpredictably.
Equity securities may decline in value due to factors affecting equity
securities markets generally, particular industries represented in those markets
or the issuer itself.

The Fund makes substantial use of short sales for investment and risk management
purposes, including when Analytic anticipates that the market price of
securities will decline or will underperform relative to other securities held
in the Fund's portfolio. The Fund intends to take short equity positions in an
amount equal to approximately 30% of the Fund's net assets at the time of sale,
but reserves the flexibility to hold short positions of up 70% of net assets.
Short sales are transactions in which the Fund sells a security or other
instrument (such as an option, forward, futures or other derivative contract)
that it does not own. When the Fund engages in a short sale on a security, it
must borrow the security sold short and deliver it to the counterparty. The Fund
will ordinarily have to pay a fee or premium to borrow particular securities and
be obligated to repay the lender of the security any dividends or interest that
accrue on the security during the period of the loan. The amount of any gain
from a short sale will be decreased, and the amount of any loss increased, by
the amount of the premium, dividends, interest or expenses the Fund pays in
connection with the short sale. Short sales expose the Fund to the risk that it
will be required to cover its short position at a time when the securities have
appreciated in value, thus resulting in a potentially unlimited loss to the
Fund.

The distributions shareholders receive from the Fund are based primarily on the
dividends it earns from its equity investments as well as the gains the Fund
receives from writing options and using other derivative instruments, closing
out short sales and selling portfolio securities, each of which can vary widely
over the short and long term. The dividend income from the Fund's investments in
equity securities will be influenced by both general economic activity and
issuer-specific factors. In the event of a recession or adverse events affecting
a specific industry or issuer, an issuer of equity securities held by the Fund
may reduce the dividends paid on such securities. If prevailing market interest
rates decline, interest rates on any debt instruments held by the Fund, and
shareholders' income from the Fund, would likely decline as well.

There are various risks associated with the Option Strategy. The purchaser of an
index option written by the Fund has the right to any appreciation in the cash
value of the index over the strike price on the expiration date. Therefore, as
the writer of an index call option; the Fund forgoes the opportunity to profit
from increases in the index over the strike price of the option. However, the
Fund has retained the risk of loss (net of premiums received) should the price
of the Fund's portfolio securities decline. Similarly, as the writer of a call
option on an individual security held in the Fund's portfolio, the Fund forgoes,
during the option's life, the opportunity to profit from increases in the market
value of the security covering the call option above the sum of the premium and
the strike price of the call but has retained the risk of loss (net of premiums
received) should the price of the underlying security decline. The value of
options written by the Fund, which will be priced daily, will be affected by,
among other factors, changes in the value of underlying securities (including
those comprising an index), changes in the dividend rates of underlying
securities, changes in interest rates, changes in the actual or perceived
volatility of the stock market and underlying securities and the remaining time
to an option's expiration. The value of an option also may be adversely affected
if the market for the option is reduced or becomes less liquid.

An investment in the Fund is subject to certain risks and other considerations,
including, but not limited to: Equity Risk; Short Sale Risk; Options Risk,
Management Risk; Tax Treatment of Distributions; Derivatives Risk; Counterparty
Risk; Credit Risk; Income Risk; Medium- and Smaller-Company Risk; Focused
Investment Risk; Interest Rate Risk; Liquidity Risk; Market Disruption and
Geopolitical Risk; Leverage Risk; Foreign Investment Risk; Other Investment
Companies Risk; and Inflation/Deflation Risk.



8 | Semiannual Report | June 30, 2009


OLA | Old Mutual/Claymore Long-Short Fund

Fund SUMMARY | AS OF JUNE 30, 2009 (unaudited)

FUND STATISTICS
---------------------------------------------------------------
Share Price                                               $7.66
Common Share Net Asset Value                              $9.35
Premium/(Discount) to NAV                               -18.07%
Net Assets ($000)                                      $177,783
---------------------------------------------------------------


TOTAL RETURNS
---------------------------------------------------------------
(INCEPTION 8/25/05)                   MARKET                NAV
---------------------------------------------------------------
Six Months                             4.25%             -2.20%
One Year                             -31.50%            -29.36%
Three Year - average annual          -12.16%            -11.01%
Since Inception - average annual     -12.90%             -8.34%
---------------------------------------------------------------


SECTOR BREAKDOWN                                             %*
---------------------------------------------------------------
Information Technology                                    20.9%
Financials                                                16.3%
Health Care                                               14.1%
Energy                                                    12.3%
Consumer Discretionary                                    10.2%
Consumer Staples                                           9.3%
Industrials                                                8.7%
Telecommunications                                         3.2%
Utilities                                                  2.5%
Materials                                                  2.5%
---------------------------------------------------------------
* % of long-term investments and securities sold short

Securities are classified by sectors that represent broad groupings of related
industries.


TOP TEN                                                % OF NET
LONG-TERM COMMON STOCKS                                  ASSETS
---------------------------------------------------------------
Exxon Mobil Corp.                                          4.3%
Intel Corp.                                                2.7%
Chevron Corp.                                              2.5%
Hewlett-Packard Co.                                        2.5%
Comcast Corp. - Class A                                    2.4%
Microsoft Corp.                                            2.3%
Occidental Petroleum Corp.                                 2.2%
AT&T, Inc.                                                 2.1%
Corning, Inc.                                              1.9%
PPL Corp.                                                  1.9%
---------------------------------------------------------------


                                                       % OF NET
TOP FIVE SECURITIES SOLD SHORT                           ASSETS
---------------------------------------------------------------
Plains Exploration & Production Co.                        1.0%
El Paso Corp.                                              0.9%
AutoZone, Inc.                                             0.8%
King Pharmaceuticals, Inc.                                 0.8%
DaVita, Inc.                                               0.8%
---------------------------------------------------------------
Past performance does not guarantee future results. All portfolio data is
subject to change daily. For more current information, please visit
www.claymore.com/ola. The above summaries are provided for informational
purposes only and should not be viewed as recommendations.


Line chart:

SHARE PRICE & NAV PERFORMANCE

       Share Price     NAV

6/30/08 $13.23       $15.19
         13.16        15.05
         12.88        14.87
         12.75        15.03
         12.76        14.99
         12.97        15.07
         12.9         15.02
         12.93        15.08
         12.68        14.83
         12.3         14.88
         12.19        14.72
         12.45        14.77
         12.64        14.83
         12.66        14.89
         12.8         14.93
         12.96        14.71
         12.75        14.55
         12.36        14.51
         12.55        14.82
         12.5         14.76
         12.67        14.78
         12.95        14.87
         12.89        14.77
         12.78        14.65
         12.54        14.64
         12.73        14.76
         12.75        14.67
         12.41        14.76
         12.77        14.68
         12.64        14.58
         12.45        14.68
         12.41        14.8
         12.56        14.82
         12.55        14.67
         12.47        14.51
         12.39        14.53
         12.47        14.68
         12.49        14.79
         12.65        14.85
         12.47        14.72
         12.44        14.64
         12.53        14.75
         12.67        14.9
         12.66        14.8
         12.71        14.7
         12.66        14.5
         12.34        14.23
         12.35        14.13
         12.4         14.31
         12.01        14.12
         12.15        14.21
         11.66        13.89
         11.54        13.94
         10.93        13.58
         10.71        13.61
         10.28        12.99
         10.35        13.28
         10.98        13.72
         10.63        13.53
         10.49        13.28
         10.39        13.11
         10.49        13.36
         10.4         13.31
         9.75         12.36
         10.1         12.83
         10.23        12.86
         10.05        12.42
         10.03        12.51
         9.05         11.92
         8.44         11.45
         7.9          11.28
         7.09          10.6
         6.85         10.48
         8.01         11.63
         8.4          11.45
         7.94         10.52
         8.36         10.78
         8.46         10.76
         9.02         11.22
         8.88         11.12
         8.5          10.75
         8.48         10.97
         8.35         10.82
         8.45         10.67
         9.18         11.29
         9.23         11.04
         9.36         11.12
         9.45         11.33
         9.44         11.35
         9.73         11.52
         9.35         11.15
         8.93         10.82
         9.1             11
         9.02         10.98
         8.75         10.92
         8.38         10.52
         8.48         10.84
         8.27         10.54
         8.15         10.35
         8.01          10.4
         7.29          9.98
         6.43          9.59
         6.6             10
         7.5           9.86
         7.37          9.87
         7.6          10.07
         7.82         10.21
         7.14          9.74
         7.29          9.95
         7.6          10.04
         7.3           9.92
         7.45         10.13
         7.75          10.3
         7.6          10.21
         7.86         10.32
         7.36          9.77
         7.49           9.8
         7.51          9.72
         7.8          10.03
         7.63         10.01
         7.53          9.86
         7.53          9.97
         7.54          9.77
         7.42          9.75
         7.75          9.79
         7.76          9.83
         7.65          9.85
         7.8          10.04
         7.98         10.24
         8.36         10.34
         8.45          10.3
         8.68         10.46
         8.55         10.35
         8.62         10.43
         8.67         10.39
         8.6          10.21
         8.61         10.21
         8.27          9.94
         8.08         10.02
         8.28         10.12
         7.95           9.7
         8.16          9.97
         8.17          9.91
         8.2           9.89
         8.24          9.98
         8.37         10.07
         8.52         10.29
         8.35         10.03
         8.32          9.97
         8.41          9.98
         8.65         10.14
         8.5          10.11
         8.52         10.14
         8.69         10.25
         8.59         10.37
         8.36         10.07
         8.36         10.03
         8.27         10.07
         8.2          10.03
         7.85          9.65
         7.75          9.68
         7.69          9.63
         7.49          9.49
         7.14          9.26
         7.5           9.43
         7.57           9.3
         7.41          9.23
         7.27          9.13
         6.66           8.8
         6.68          8.84
         6.96          9.04
         6.54          8.65
         6.45          8.64
         6.35           8.6
         6.71          8.95
         6.5           8.53
         6.82          8.71
         6.86          8.75
         6.91          8.79
         7.1           8.85
         7.14           8.7
         7.03           8.9
         7.01          8.76
         7.42          9.02
         7.18          9.01
         7.3           8.98
         7.4           9.07
         7.31          9.04
         7.08          8.93
         7.33          9.03
         7.45          9.08
         7.6           9.22
         7.59          9.17
         7.47          9.26
         7.5           9.22
         7.54          9.32
         7.71          9.23
         7.66          9.09
         7.41          9.18
         7.43          9.12
         7.54          9.13
         7.54          9.08
         7.26          9.11
         7.43          9.18
         7.49          9.17
         7.69          9.22
         7.65          9.17
         7.45          9.23
         7.57          9.22
         7.7           9.29
         7.72          9.28
         7.75          9.29
         7.93          9.18
         7.76          9.24
         7.82           9.2
         7.69          9.24
         7.82          9.12
         7.51          9.13
         7.6            9.3
         7.53          9.25
         7.5           9.31
         7.44          9.25
         7.63          9.42
         7.79          9.41
         7.77          9.44
         7.6           9.36
         7.69          9.39
         7.8           9.46
         7.75          9.41
         7.76          9.44
         7.92          9.47
         8.12          9.59
         8.11          9.51
         7.93          9.45
         7.95          9.45
         7.93          9.49
         7.81          9.49
         7.89          9.56
         7.91          9.56
         7.79          9.37
         7.73          9.41
         7.68          9.29
         7.56          9.25
         7.54          9.29
         7.55          9.32
         7.53          9.35
         7.43          9.13
         7.42          9.18
         7.54          9.23
         7.73          9.31
         7.68          9.33
         7.73          9.37
6/30/09  7.66          9.35


Bar Chart:

Distributions to Shareholders

Mar 08   $0.4
Jun 08   $0.4
Sep 08   $0.4
Dec 08   $0.4
Mar 09   $0.4
Jun 09   $0.24


                                                       % OF NET
FUND BREAKDOWN                                           ASSETS
---------------------------------------------------------------
Long-Term Investments                                    117.3%
Short-Term Investments                                    10.9%
---------------------------------------------------------------
Total Investments                                        128.2%
Securities Sold Short                                    -28.1%
Total Value of Options Written                            -2.6%
Other Assets less Liabilities                              2.5%
---------------------------------------------------------------
Total Net Assets                                         100.0%
---------------------------------------------------------------

                                           Semiannual Report | June 30, 2009 | 9



OLA | Old Mutual/Claymore Long-Short Fund

Portfolio of INVESTMENTS | JUNE 30, 2009 (unaudited)

NUMBER
OF SHARES                                                                 VALUE
================================================================================

             LONG-TERM INVESTMENTS - 117.3%
             CONSUMER DISCRETIONARY - 11.0%
      5,990  Amazon.com, Inc. (a) (b)                              $    501,123
      2,148  Barnes & Noble, Inc.                                        44,313
      7,601  Best Buy Co., Inc. (b)                                     254,558
     25,248  Big Lots, Inc. (a)                                         530,966
     32,198  Brinker International, Inc.                                548,332
     13,276  Carmax, Inc. (a)                                           195,157
      2,442  Centex Corp.                                                20,659
    291,835  Comcast Corp. - Class A (b)                              4,228,689
     12,947  Dillard's, Inc. - Class A (c)                              119,112
     10,292  DIRECTV Group, Inc. (a) (b)                                254,315
     65,380  DISH Network Corp. - Class A (a)                         1,059,810
     86,755  Ford Motor Co. (a) (b)                                     526,603
     72,129  Gap, Inc. (b)                                            1,182,916
     11,024  Guess? Inc.                                                284,199
     71,898  H&R Block, Inc. (b)                                      1,238,803
     42,327  Interpublic Group of Companies, Inc. (a) (b)               213,751
     18,541  JC Penney Co., Inc. (c)                                    532,312
     27,756  Johnson Controls, Inc. (b)                                 602,860
     82,875  Las Vegas Sands Corp. (a)                                  651,398
     15,129  Liberty Global, Inc. - Class A (a)                         240,400
     17,109  Lowe's Cos., Inc. (c)                                      332,086
     27,414  Marriott International, Inc. - Class A (b)                 605,034
     11,504  McGraw-Hill Cos., Inc. (b)                                 346,385
      4,196  Office Depot, Inc. (a)                                      19,134
     62,051  RadioShack Corp.                                           866,232
     50,882  Starbucks Corp. (a) (b)                                    706,751
     12,575  Target Corp. (c)                                           496,335
     22,892  TJX Cos., Inc. (b)                                         720,182
          1  WABCO Holdings, Inc.                                            18
     95,815  Walt Disney Co. (b)                                      2,235,364
      4,474  Williams-Sonoma, Inc.                                       53,106
--------------------------------------------------------------------------------
                                                                     19,610,903
--------------------------------------------------------------------------------

             CONSUMER STAPLES - 12.1%
     10,917  BJ's Wholesale Club, Inc. (a)                              351,855
     28,433  Brown-Forman Corp. - Class B (c)                         1,222,050
     17,997  Bunge Ltd. (Bermuda)                                     1,084,319
     14,646  Coca-Cola Enterprises, Inc.                                243,856
     50,649  Costco Wholesale Corp. (b)                               2,314,659
     46,180  Dean Foods Co. (a) (b)                                     886,194
     27,365  Estee Lauder Cos., Inc. - Class A (b)                      894,015


NUMBER
OF SHARES                                                                 VALUE
================================================================================
             CONSUMER STAPLES (CONTINUED)
      1,644  Hormel Foods Corp. (b)                                $     56,784
      1,385  Kroger Co. (c)                                              30,539
      2,683  Pepsi Bottling Group, Inc.                                  90,793
     16,152  PepsiCo, Inc. (b)                                          887,714
     75,789  Philip Morris International, Inc. (b)                    3,305,916
     21,277  Procter & Gamble Co. (b)                                 1,087,255
     29,358  Safeway, Inc. (b)                                          598,022
    133,516  Sara Lee Corp. (b)                                       1,303,116
    130,365  SYSCO Corp. (b)                                          2,930,605
    177,229  Tyson Foods, Inc. - Class A (b)                          2,234,858
     68,375  Walgreen Co. (b)                                         2,010,225
--------------------------------------------------------------------------------
                                                                     21,532,775
--------------------------------------------------------------------------------

             ENERGY - 15.1%
     15,536  Anadarko Petroleum Corp. (b)                               705,179
      1,360  Apache Corp. (b)                                            98,124
     16,324  Baker Hughes, Inc. (b)                                     594,846
     28,890  Cabot Oil & Gas Corp. (c)                                  885,190
      3,827  Cameron International Corp. (a) (c)                        108,304
     67,008  Chevron Corp. (b)                                        4,439,280
     30,465  ConocoPhillips (c)                                       1,281,358
      3,837  EOG Resources, Inc. (b)                                    260,609
    108,422  Exxon Mobil Corp. (b)                                    7,579,782
     29,617  Halliburton Co. (b)                                        613,072
     36,744  Hess Corp. (c)                                           1,974,990
     18,028  Marathon Oil Corp. (b)                                     543,184
     36,649  Murphy Oil Corp. (b)                                     1,990,774
     58,717  Occidental Petroleum Corp. (c)                           3,864,166
      1,425  Peabody Energy Corp.                                        42,978
     47,635  Pioneer Natural Resources Co. (b)                        1,214,692
     30,912  Rowan Cos., Inc.                                           597,220
--------------------------------------------------------------------------------
                                                                     26,793,748
--------------------------------------------------------------------------------

             FINANCIALS - 16.6%
        254  Aflac, Inc. (b)                                              7,897
        324  Alexandria Real Estate Equities, Inc. - REIT                11,596
      3,923  Allied World Assurance Co. Holdings Ltd. (Bermuda)         160,176
     57,817  American Express Co. (b)                                 1,343,667
        387  American Financial Group, Inc.                               8,351
         17  Apartment Investment & Management Co. - Class A - REIT         150
      5,978  Assurant, Inc. (b)                                         144,010
    200,133  Bank of America Corp. (c)                                2,641,756
     25,579  Bank of Hawaii Corp.                                       916,496

See notes to financial statements.

10 | Semiannual Report | June 30, 2009


OLA | Old Mutual/Claymore Long-Short Fund | PORTFOLIO OF INVESTMENTS (unaudited)
continued

NUMBER
OF SHARES                                                                 VALUE
================================================================================

             FINANCIALS (CONTINUED)
     81,966  Bank of New York Mellon Corp. (c)                     $  2,402,423
     27,780  BB&T Corp. (b)                                             610,604
      7,533  BlackRock, Inc.                                          1,321,439
      5,410  BOK Financial Corp.                                        203,795
    156,970  Charles Schwab Corp. (c)                                 2,753,254
     16,495  Chubb Corp. (b)                                            657,821
     29,757  Cincinnati Financial Corp. (b)                             665,069
      2,005  Citigroup, Inc.                                              5,955
     73,028  Discover Financial Services (c)                            749,998
      3,998  Federated Investors, Inc. - Class B (b)                     96,312
     25,881  Franklin Resources, Inc. (c)                             1,863,691
      4,469  Hospitality Properties Trust - REIT                         53,136
     99,030  Hudson City Bancorp, Inc. (b)                            1,316,109
     27,716  Invesco Ltd. (Bermuda)                                     493,899
      7,037  Janus Capital Group, Inc. (b)                               80,222
      6,487  JPMorgan Chase & Co. (c)                                   221,272
     27,220  Kimco Realty Corp. - REIT (b)                              273,561
     82,001  MBIA, Inc. (a)                                             355,064
      2,282  MetLife, Inc. (b)                                           68,483
          2  New York Community Bancorp, Inc.                                21
     30,317  Northern Trust Corp. (c)                                 1,627,416
     12,083  Principal Financial Group, Inc. (b)                        227,644
          2  Progressive Corp. (a) (b)                                       30
     21,965  Public Storage - REIT (b)                                1,438,268
     12,282  Rayonier, Inc. - REIT (b) (c)                              446,451
      3,383  SL Green Realty Corp. - REIT                                77,606
     13,014  State Street Corp. (b)                                     614,261
     52,555  T Rowe Price Group, Inc. (c)                             2,189,967
        593  TD Ameritrade Holding Corp. (a)                             10,401
          2  TFS Financial Corp.                                             21
     25,000  Torchmark Corp. (b)                                        926,000
      2,399  Unum Group                                                  38,048
    108,103  US Bancorp. (b)                                          1,937,206
     24,002  Wells Fargo & Co. (b)                                      582,288
--------------------------------------------------------------------------------
                                                                     29,541,834
--------------------------------------------------------------------------------

             HEALTH CARE - 16.4%
     21,419  Aetna, Inc. (c)                                            536,546
    160,483  AmerisourceBergen Corp. (b)                              2,846,968
     38,109  Amgen, Inc. (a) (b)                                      2,017,490
     10,127  Becton Dickinson & Co. (b)                                 722,156
     21,073  Biogen Idec, Inc. (a)                                      951,446
     29,508  Cardinal Health, Inc. (b)                                  901,469
     45,036  Coventry Health Care, Inc. (a) (b)                         842,624


NUMBER
OF SHARES                                                                 VALUE
================================================================================

             HEALTH CARE (CONTINUED)
     15,030  Express Scripts, Inc. (a) (b)                         $  1,033,313
     22,458  Forest Laboratories, Inc. (a) (b)                          563,920
     39,196  Gilead Sciences, Inc. (a) (b)                            1,835,941
     30,192  Health Net, Inc. (a)                                       469,486
     17,990  Hill-Rom Holdings, Inc.                                    291,798
      9,631  Humana, Inc. (a) (c)                                       310,696
        117  Illumina, Inc. (a)                                           4,556
     26,628  IMS Health, Inc. (c)                                       338,176
     52,035  Johnson & Johnson (c)                                    2,955,588
     63,650  McKesson Corp. (c)                                       2,800,600
      4,673  Medco Health Solutions, Inc. (a) (c)                       213,136
     41,416  Merck & Co, Inc. (b)                                     1,157,991
    132,536  Pfizer, Inc. (b)                                         1,988,040
     31,983  Schering-Plough Corp. (b)                                  803,413
     42,627  Stryker Corp. (c)                                        1,693,997
    257,415  Tenet Healthcare Corp. (a) (c)                             725,910
     27,342  UnitedHealth Group, Inc. (b)                               683,003
     12,475  Varian Medical Systems, Inc. (a) (b)                       438,372
     26,192  Wyeth (c)                                                1,188,855
     20,247  Zimmer Holdings, Inc. (a) (b)                              862,522
--------------------------------------------------------------------------------
                                                                     29,178,012
--------------------------------------------------------------------------------
             INDUSTRIALS - 10.6%
          1  Aecom Technology Corp. (a)                                      32
     49,340  AGCO Corp. (a) (b)                                       1,434,314
      7,616  C.H. Robinson Worldwide, Inc. (b)                          397,174
      3,001  Copa Holdings SA - Class A (Panama)                        122,501
     17,783  CSX Corp. (b)                                              615,825
     11,963  Cummins, Inc. (b)                                          421,217
     52,893  Fluor Corp. (c)                                          2,712,882
     32,234  General Dynamics Corp. (b)                               1,785,441
     14,510  Harsco Corp.                                               410,633
        390  ITT Corp.                                                   17,355
     26,425  Jacobs Engineering Group, Inc. (a) (c)                   1,112,228
      5,293  Joy Global, Inc.                                           189,066
    107,101  KBR, Inc.                                                1,974,942
     17,364  Lockheed Martin Corp. (c)                                1,400,407
        717  Pall Corp. (b)                                              19,044
     42,604  Raytheon Co. (b)                                         1,892,896
     17,968  Shaw Group, Inc. (a)                                       492,503
    199,224  Southwest Airlines Co.                                   1,340,778
     10,273  Timken Co.                                                 175,463
     10,041  Tyco International Ltd. (Bermuda) (b)                      260,865
      4,934  Union Pacific Corp. (b)                                    256,864


See notes to financial statements.

                                          Semiannual Report | June 30, 2009 | 11



OLA | Old Mutual/Claymore Long-Short Fund | PORTFOLIO OF INVESTMENTS (unaudited)
continued

NUMBER
OF SHARES                                                                 VALUE
================================================================================
             INDUSTRIALS (CONTINUED)
      8,348  United Technologies Corp. (c)                         $    433,762
     52,095  Waste Management, Inc. (b)                               1,466,995
--------------------------------------------------------------------------------
                                                                     18,933,187
--------------------------------------------------------------------------------

             INFORMATION TECHNOLOGY - 24.9%
     13,043  Accenture Ltd. - Class A (Bermuda)                         436,419
     30,530  Agilent Technologies, Inc. (a) (b)                         620,064
     78,379  Analog Devices, Inc. (b)                                 1,942,232
          8  AVX Corp.                                                       79
     59,050  Cisco Systems, Inc. (a) (b)                              1,100,692
     22,700  Computer Sciences Corp. (a) (b)                          1,005,610
      9,016  Compuware Corp. (a) (b)                                     61,850
     46,245  Convergys Corp. (a) (b)                                    429,154
    208,550  Corning, Inc. (c)                                        3,349,313
     63,991  Dell, Inc. (a) (c)                                         878,596
    103,912  eBay, Inc. (a) (b)                                       1,780,013
     70,766  Electronic Arts, Inc. (a) (c)                            1,537,038
      1,786  Google, Inc. - Class A (a) (c)                             752,960
      6,938  Hewitt Associates, Inc. - Class A (a)                      206,614
    114,578  Hewlett-Packard Co. (b)                                  4,428,440
     32,965  Ingram Micro, Inc. - Class A (a)                           576,888
    286,580  Intel Corp. (b)                                          4,742,899
     20,893  International Business Machines Corp. (b)                2,181,647
     53,635  Lexmark International, Inc. - Class A (a) (b)              850,115
     27,183  LSI Corp. (a)                                              123,954
      6,423  Mastercard, Inc. - Class A (b)                           1,074,632
    172,008  Microsoft Corp. (b)                                      4,088,630
    392,741  Motorola, Inc. (b)                                       2,603,873
     28,112  QUALCOMM, Inc. (b)                                       1,270,662
     14,655  Sun Microsystems, Inc. (a)                                 135,119
     28,644  Tech Data Corp. (a)                                        936,945
         68  Teradata Corp. (a) (c)                                       1,593
    144,210  Texas Instruments, Inc. (b)                              3,071,673
     23,246  Total System Services, Inc.                                311,264
      3,338  VeriSign, Inc. (a)                                          61,686
     34,617  Visa, Inc. - Class A                                     2,155,254
     58,231  Western Union Co. (b)                                      954,988
     35,808  Yahoo!, Inc. (a) (b)                                       560,753
--------------------------------------------------------------------------------
                                                                     44,231,649
--------------------------------------------------------------------------------


NUMBER
OF SHARES                                                                 VALUE
================================================================================

             MATERIALS - 3.1%
      3,371  Ashland, Inc. (b)                                     $     94,557
        950  CF Industries Holdings, Inc.                                70,433
      9,791  Cliffs Natural Resources, Inc.                             239,586
          3  Commercial Metals Co.                                           48
     44,664  Dow Chemical Co. (c)                                       720,877
     17,018  Eastman Chemical Co. (c)                                   644,982
     45,945  Ecolab, Inc. (b)                                         1,791,396
     23,705  Huntsman Corp.                                             119,236
     12,978  International Paper Co.                                    196,357
     40,923  MeadWestvaco Corp. (c)                                     671,546
      4,745  Pactiv Corp. (a)                                           102,967
      8,556  Terra Industries, Inc.                                     207,226
     17,421  Titanium Metals Corp. (b)                                  160,099
     13,642  United States Steel Corp. (c)                              487,565
--------------------------------------------------------------------------------
                                                                      5,506,875
--------------------------------------------------------------------------------

             TELECOMMUNICATIONS - 4.0%
    149,549  AT&T, Inc. (b)                                           3,714,797
      2,801  Embarq Corp.                                               117,810
     65,044  NII Holdings, Inc. (a)                                   1,240,389
    358,760  Sprint Nextel Corp. (a) (c)                              1,725,636
      7,576  United States Cellular Corp. (a)                           291,297
--------------------------------------------------------------------------------
                                                                      7,089,929
--------------------------------------------------------------------------------

             UTILITIES - 3.5%
     31,545  AES Corp. (a) (b)                                          366,237
     18,084  Dynegy, Inc. - Class A (a)                                  41,051
     15,059  Energen Corp.                                              600,854
     71,474  NRG Energy, Inc. (a)                                     1,855,465
    100,683  PPL Corp. (c)                                            3,318,512
--------------------------------------------------------------------------------
                                                                      6,182,119
--------------------------------------------------------------------------------

             TOTAL LONG-TERM INVESTMENTS - 117.3%
             (Cost $242,627,791)                                    208,601,031
--------------------------------------------------------------------------------

PRINCIPAL
AMOUNT                                                                    VALUE
================================================================================
             U.S. GOVERNMENT SECURITIES - 7.6%
$13,550,000  U.S. Treasury Bill
             yielding 0.351% 2/11/10 maturity
             (Cost $13,520,359)                                      13,519,350
--------------------------------------------------------------------------------


See notes to financial statements.

12 | Semiannual Report | June 30, 2009



OLA | Old Mutual/Claymore Long-Short Fund | PORTFOLIO OF INVESTMENTS (unaudited)
continued


NUMBER
OF SHARES                                                                 VALUE
================================================================================

             MONEY MARKET FUNDS - 3.3%
  5,776,474  Dreyfus Institutional Reserve Money Market Fund
             (Cost $5,776,474)                                     $  5,776,474
--------------------------------------------------------------------------------
             TOTAL SHORT-TERM INVESTMENTS - 10.9%
             (Cost $19,296,833)                                      19,295,824
--------------------------------------------------------------------------------
             TOTAL INVESTMENTS - 128.2%
             (Cost $261,924,624)                                    227,896,855
             Securities Sold Short - (28.1%)
             (Proceeds $43,501,191)                                 (49,961,578)
             Total Value of Options Written
             (Premiums received $4,584,152) - (2.6%)                 (4,579,525)
             Other Assets in excess of Liabilities  - 2.5%            4,427,207
--------------------------------------------------------------------------------
             NET ASSETS  - 100.0%                                  $177,782,959
================================================================================


             SECURITIES SOLD SHORT - 28.1%
             COMMON STOCKS - 27.0%
             CONSUMER DISCRETIONARY - 3.0%
     13,898  Abercrombie & Fitch Co. - Class A                     $    352,870
      9,549  AutoZone, Inc.                                           1,442,949
      4,300  Black & Decker Corp.                                       123,238
      7,266  CBS Corp. - Class B                                         50,281
     27,456  Central European Media Enterprises Ltd. - Class A
                (Bermuda)                                               540,609
     33,109  Gannett Co., Inc.                                          118,199
        659  Harman International Industries, Inc.                       12,389
     13,999  Jarden Corp.                                               262,481
      6,240  KB Home                                                     85,363
      4,113  MDC Holdings, Inc.                                         123,843
     25,293  O'Reilly Automotive, Inc.                                  963,158
     48,860  Toll Brothers, Inc.                                        829,154
     14,583  Weight Watchers International, Inc.                        375,804
--------------------------------------------------------------------------------
                                                                      5,280,338
--------------------------------------------------------------------------------

             CONSUMER STAPLES - 1.3%
     17,085  Clorox Co.                                                 953,855
      1,016  Energizer Holdings, Inc.                                    53,076
     28,856  JM Smucker Co.                                           1,404,133
--------------------------------------------------------------------------------
                                                                      2,411,064
--------------------------------------------------------------------------------

             ENERGY - 2.9%
     30,664  Chesapeake Energy Corp.                                    608,067
      2,158  Diamond Offshore Drilling, Inc.                            179,222
    173,341  El Paso Corp.                                            1,599,937
          2  Helix Energy Solutions Group, Inc.                              22
     10,198  Newfield Exploration Co.                                   333,169
     66,832  Plains Exploration & Production Co.                      1,828,523
     63,324  Quicksilver Resources, Inc.                                588,280
          2  SandRidge Energy, Inc.                                          17
--------------------------------------------------------------------------------
                                                                      5,137,237
--------------------------------------------------------------------------------


NUMBER
OF SHARES                                                                 VALUE
================================================================================

             FINANCIALS - 6.9%
      4,175  Affiliated Managers Group, Inc.                       $    242,943
     44,826  Allstate Corp.                                           1,093,754
     23,248  Ameriprise Financial, Inc.                                 564,229
    101,276  Apartment Investment & Management Co. -
                 Class A - REIT                                         896,293
     21,132  Capital One Financial Corp.                                462,368
     59,149  CB Richard Ellis Group, Inc. - Class A                     553,635
     28,155  Comerica, Inc.                                             595,478
          1  Fidelity National Financial, Inc. - Class A                     14
     60,684  First Horizon National Corp.                               728,208
     55,587  Genworth Financial, Inc. - Class A                         388,553
     58,410  Hartford Financial Services Group, Inc.                    693,327
     40,331  Huntington Bancshares, Inc.                                168,584
     21,591  Jefferies Group, Inc.                                      460,536
     31,354  Keycorp                                                    164,295
     30,985  Legg Mason, Inc.                                           755,414
     17,486  Leucadia National Corp.                                    368,780
        905  Lincoln National Corp.                                      15,575
      1,254  Markel Corp.                                               353,252
          1  NASDAQ OMX Group, Inc.                                          21
     15,877  ProLogis - REIT                                            127,969
     21,797  Protective Life Corp.                                      249,358
     11,525  Prudential Financial, Inc.                                 428,960
      1,477  Regions Financial Corp.                                      5,967
      4,310  RenaissanceRe Holdings Ltd. (Bermuda)                      200,587
    131,774  SLM Corp.                                                1,353,319
        650  St. Joe Co.                                                 17,218
     23,381  Synovus Financial Corp.                                     69,909
      7,723  Taubman Centers, Inc. - REIT                               207,440
          1  UDR, Inc. - REIT                                                10
      8,662  Vornado Realty Trust - REIT                                390,050
     56,157  XL Capital Ltd. - Class A (Cayman Islands)                 643,559
        444  Zions Bancorporation                                         5,133
--------------------------------------------------------------------------------
                                                                     12,204,738
--------------------------------------------------------------------------------

             HEALTH CARE - 4.1%
      8,582  BioMarin Pharmaceutical, Inc.                              133,965
     28,880  DaVita, Inc.                                             1,428,405
      2,867  HLTH Corp.                                                  37,558
     77,864  Hologic, Inc.                                            1,108,005
     11,709  Inverness Medical Innovations, Inc.                        416,606
     15,572  Kinetic Concepts, Inc.                                     424,337
    149,646  King Pharmaceuticals, Inc.                               1,441,091
     11,184  Laboratory Corp. of America Holdings                       758,163
      8,634  Perrigo Co.                                                239,852


See notes to financial statements.

                                          Semiannual Report | June 30, 2009 | 13



OLA | Old Mutual/Claymore Long-Short Fund | PORTFOLIO OF INVESTMENTS (unaudited)
continued


NUMBER
OF SHARES                                                                 VALUE
================================================================================

             HEALTH CARE (CONTINUED)
     35,972  Vertex Pharmaceuticals, Inc.                          $  1,282,042
        600  WellCare Health Plans, Inc.                                 11,094
--------------------------------------------------------------------------------
                                                                      7,281,118
--------------------------------------------------------------------------------

             INDUSTRIALS - 2.0%
     61,680  AMR Corp.                                                  247,954
     15,596  Avery Dennison Corp.                                       400,505
      9,191  BE Aerospace, Inc.                                         131,983
     14,850  Boeing Co.                                                 631,125
        780  Continental Airlines, Inc. - Class B                         6,911
      1,621  Delta Air Lines, Inc.                                        9,386
      8,570  Dun & Bradstreet Corp.                                     695,970
        390  FTI Consulting, Inc.                                        19,781
     13,965  Iron Mountain, Inc.                                        401,494
     50,825  Manitowoc Co., Inc.                                        267,339
     23,024  Oshkosh Corp.                                              334,769
     19,276  Owens Corning                                              246,347
      2,425  Rockwell Automation, Inc.                                   77,891
        207  Terex Corp.                                                  2,498
      4,685  Textron, Inc.                                               45,257
--------------------------------------------------------------------------------
                                                                      3,519,210
--------------------------------------------------------------------------------

             INFORMATION TECHNOLOGY - 5.4%
     10,694  Applied Materials, Inc.                                    117,313
      3,710  BMC Software, Inc.                                         125,361
     14,310  Brocade Communications Systems, Inc.                       111,904
     85,153  Ciena Corp.                                                881,334
      7,137  Citrix Systems, Inc.                                       227,599
    115,851  Cypress Semiconductor Corp.                              1,065,829
      2,816  F5 Networks, Inc.                                           97,405
      5,131  Fidelity National Information Services, Inc.               102,415
     26,347  Fiserv, Inc.                                             1,204,058
     17,910  International Rectifier Corp.                              265,247
      3,353  Itron, Inc.                                                184,650
     43,840  KLA-Tencor Corp.                                         1,106,960
     48,068  Lam Research Corp.                                       1,249,768
     60,050  Linear Technology Corp.                                  1,402,167
     28,994  Novellus Systems, Inc.                                     484,200
     55,406  Nuance Communications, Inc.                                669,858
     26,485  Rambus, Inc.                                               410,253
--------------------------------------------------------------------------------
                                                                      9,706,321
--------------------------------------------------------------------------------


NUMBER
OF SHARES                                                                 VALUE
================================================================================
             MATERIALS - 0.5%
          1  Eagle Materials, Inc.                                 $         25
     23,105  International Flavors & Fragrances, Inc.                   755,996
      6,563  Weyerhaeuser Co.                                           199,712
--------------------------------------------------------------------------------
                                                                        955,733
--------------------------------------------------------------------------------

             TELECOMMUNICATIONS - 0.7%
     10,163  Leap Wireless International, Inc.                          334,668
     34,824  SBA Communications Corp. - Class A                         854,581
--------------------------------------------------------------------------------
                                                                      1,189,249
--------------------------------------------------------------------------------

             UTILITIES - 0.2%
      8,030  Consolidated Edison, Inc.                                  300,483
--------------------------------------------------------------------------------

             TOTAL COMMON STOCKS SOLD SHORT - 27.0 %
             (Proceeds $41,617,858)                                  47,985,491
--------------------------------------------------------------------------------

             TRACKING STOCKS - 0.9%
             CONSUMER DISCRETIONARY - 0.9%
     27,883  Liberty Media Corp. - Capital Series A                     378,093
     44,209  Liberty Media Corp. - Entertainment Series A             1,182,591
--------------------------------------------------------------------------------
             (Proceeds $1,461,779)                                    1,560,684
--------------------------------------------------------------------------------

             MASTER LIMITED PARTNERSHIPS - 0.2%
             FINANCIALS - 0.2%
     15,431  Lazard Ltd. - Class A (Bermuda)
             (Proceeds $421,554)                                        415,403
--------------------------------------------------------------------------------
             TOTAL SECURITIES SOLD SHORT - 28.1 %
             (Proceeds $43,501,191)                                $ 49,961,578
================================================================================


See notes to financial statements.

14 | Semiannual Report | June 30, 2009



OLA | Old Mutual/Claymore Long-Short Fund | PORTFOLIO OF INVESTMENTS (unaudited)
continued




CONTRACTS
(100 SHARES                                           EXPIRATION   EXERCISE       MARKET
PER CONTRACT)  OPTIONS WRITTEN(a)                           DATE      PRICE        VALUE
=========================================================================================
                                                                  
               CALL OPTIONS WRITTEN (A)
          61   ISE Intergrated Oil and Gas Index       July 2009   $ 215.00   $   22,875
       1,740   ISE SINdex                              July 2009      85.00      478,500
       5,090   KBW Bank Index                          July 2009      37.50      445,375
         360   Morgan Stanley Cyclical Index           July 2009     550.00      865,800
         260   NYSE Arca Oil Index                     July 2009     930.00      422,500
         600   S&P 100 Index                           July 2009     425.00      651,000
         585   S&P 100 Index                           July 2009     430.00      453,375
         425   S&P 400 Midcap Index                    July 2009     570.00      782,000
         145   S&P 500 Index                           July 2009     935.00      150,075
         555   S&P 600 Small Cap Index                 July 2009     270.00      308,025
-----------------------------------------------------------------------------------------
               TOTAL OPTIONS WRITTEN
               (Premiums received $4,584,152)                                 $4,579,525
-----------------------------------------------------------------------------------------


ISE - International Securities Exchange, LLC
KBW - Keefe, Bruyette & Woods, Inc.
REIT - Real Estate Investment Trust
S&P - Standard and Poor's
(a)  Non-income producing security.
(b)  All or a portion of these securities are held as collateral for securities
     sold short.
(c)  All or a portion of these securities are held as collateral for futures or
     options.

Securities are classified by sectors that represent broad groupings of related
industries.

See notes to financial statements.

                                          Semiannual Report | June 30, 2009 | 15



OLA | Old Mutual/Claymore Long-Short Fund

Statement of ASSETS AND LIABILITIES | JUNE 30, 2009 (unaudited)




                                                                                               
ASSETS
   Investments, at value (cost $242,627,791)                                                      $208,601,031
   Short term investments (cost $19,296,833)                                                        19,295,824
--------------------------------------------------------------------------------------------------------------
      Total investments (cost $261,924,624)                                                        227,896,855
--------------------------------------------------------------------------------------------------------------
   Cash                                                                                              3,477,325
   Variation margin on futures                                                                         926,977
   Dividends and interest receivable                                                                   269,277
   Other assets                                                                                         26,824
--------------------------------------------------------------------------------------------------------------
      Total assets                                                                                 232,597,258
--------------------------------------------------------------------------------------------------------------

LIABILITIES
   Securities sold short, at value (proceeds $43,501,191)                                           49,961,578
   Options written, at value (premiums received of $4,584,152)                                       4,579,525
   Advisory fee payable                                                                                146,521
   Investments purchased payable                                                                        35,284
   Administration fee payable                                                                            4,029
   Accrued expenses                                                                                     87,362
--------------------------------------------------------------------------------------------------------------
      Total liabilities                                                                             54,814,299
--------------------------------------------------------------------------------------------------------------

NET ASSETS                                                                                        $177,782,959
==============================================================================================================

COMPOSITION OF NET ASSETS
Common stock, $.01 par value per share; unlimited number of shares authorized,
   19,005,240 shares issued and outstanding                                                       $    190,052
Additional paid-in capital                                                                         320,244,358
Net unrealized depreciation on investments, futures, options,
   securities sold short, forwards and currency translation                                        (39,199,234)
Accumulated net realized loss on investments, futures, options, securities sold
   short, forwards and currency transactions                                                       (88,864,071)
Accumulated net investment loss                                                                    (14,588,146)
--------------------------------------------------------------------------------------------------------------

NET ASSETS                                                                                        $177,782,959
==============================================================================================================

NET ASSET VALUE
   (based on 19,005,240 common shares outstanding)                                                $       9.35
==============================================================================================================



See notes to financial statements.

16 | Semiannual Report | June 30, 2009



OLA | Old Mutual/Claymore Long-Short Fund

Statement of OPERATIONS | FOR THE SIX MONTHS ENDED JUNE 30, 2009 (unaudited)



                                                                             
INVESTMENT INCOME
   Dividends                                                                    $  2,788,867
   Interest                                                                           68,568
---------------------------------------------------------------------------------------------------------------
      Total income                                                                                 $ 2,857,435
---------------------------------------------------------------------------------------------------------------
EXPENSES
   Advisory fee                                                                      890,714
   Dividends on securities sold short                                                819,606
   Custodian fee                                                                     435,503
   Professional fees                                                                  82,495
   Trustees' fees and expenses                                                        71,601
   Printing expense                                                                   40,889
   Fund accounting                                                                    40,516
   Administration fee                                                                 24,495
   NYSE listing fee                                                                   10,498
   Transfer agent fee                                                                  9,380
   Insurance                                                                           9,103
   Miscellaneous                                                                       6,344
---------------------------------------------------------------------------------------------------------------
      Total expenses                                                                                 2,441,144
---------------------------------------------------------------------------------------------------------------
      NET INVESTMENT INCOME                                                                            416,291
---------------------------------------------------------------------------------------------------------------
REALIZED AND UNREALIZED GAIN (LOSS):
   Net realized gain (loss) on:
      Investments                                                                                 $(58,360,969)
      Futures                                                                                        1,374,807
      Options                                                                                       (5,235,742)
      Securities sold short                                                                         14,834,326
      Foreign currency forwards and currency transactions                                              795,401
   Net change in unrealized appreciation (depreciation) on:
      Investments                                                                                   65,128,416
      Futures                                                                                         (630,860)
      Options                                                                                       (1,728,574)
      Securities sold short                                                                        (20,082,109)
      Foreign currency forwards and currency translation                                            (1,230,842)
---------------------------------------------------------------------------------------------------------------
   NET REALIZED AND UNREALIZED LOSS                                                                 (5,136,146)
---------------------------------------------------------------------------------------------------------------
NET DECREASE IN NET ASSETS RESULTING FROM OPERATIONS                                              $ (4,719,855)
===============================================================================================================


See notes to financial statements.

                                          Semiannual Report | June 30, 2009 | 17



OLA | Old Mutual/Claymore Long-Short Fund

Statement of CHANGES IN NET ASSETS |



                                                                                             FOR THE
                                                                                    SIX MONTHS ENDED               FOR THE
                                                                                       JUNE 30, 2009            YEAR ENDED
                                                                                         (UNAUDITED)     DECEMBER 31, 2008
===========================================================================================================================
INCREASE (DECREASE) IN NET ASSETS FROM OPERATIONS
                                                                                                       
   Net investment income (loss)                                                         $    416,291         $     969,018
   Net realized gain (loss) on investments, futures, options, securities sold short,
      forwards and currency transactions                                                 (46,592,177)          (54,535,752)
   Net unrealized appreciation (depreciation) on investments, futures, options,
      securities sold short, forwards and currency translation                            41,456,031           (59,430,917)
---------------------------------------------------------------------------------------------------------------------------
      Net increase/(decrease) in net assets resulting from operations                     (4,719,855)         (112,997,651)
---------------------------------------------------------------------------------------------------------------------------
DISTRIBUTIONS TO COMMON SHAREHOLDERS
   From and in excess of net investment income                                           (12,163,354)           (2,755,313)
   Return of capital                                                                               -           (27,653,071)
---------------------------------------------------------------------------------------------------------------------------
      Total distributions to common shareholders                                         (12,163,354)          (30,408,384)
---------------------------------------------------------------------------------------------------------------------------
      Total increase (decrease) in net assets                                            (16,883,209)         (143,406,035)

NET ASSETS
   Beginning of period                                                                   194,666,168           338,072,203
---------------------------------------------------------------------------------------------------------------------------
   End of period (including accumulated net investment loss of
      $14,588,146 and $2,841,083, respectively)                                         $177,782,959         $ 194,666,168
===========================================================================================================================


See notes to financial statements.

18 | Semiannual Report | June 30, 2009


OLA | Old Mutual/Claymore Long-Short Fund

Financial HIGHLIGHTS |



                                                                                   FOR THE
                                                                          SIX MONTHS ENDED             FOR THE              FOR THE
PER SHARE OPERATING PERFORMANCE                                              JUNE 30, 2009          YEAR ENDED           YEAR ENDED
FOR A COMMON SHARE OUTSTANDING THROUGHOUT THE PERIOD                           (UNAUDITED)   DECEMBER 31, 2008    DECEMBER 31, 2007
====================================================================================================================================
                                                                                                                 
NET ASSET VALUE, BEGINNING OF PERIOD                                             $   10.24           $   17.79            $   18.89
------------------------------------------------------------------------------------------------------------------------------------
INCOME FROM INVESTMENT OPERATIONS
   Net investment income (loss)(b)                                                    0.02                0.05                (0.10)
   Net realized and unrealized gain (loss) on investments, futures, options,
      securities sold short, forwards and foreign currency                           (0.27)              (6.00)                0.60
------------------------------------------------------------------------------------------------------------------------------------
      Total from investment operations                                               (0.25)              (5.95)                0.50
------------------------------------------------------------------------------------------------------------------------------------
COMMON SHARES' OFFERING EXPENSES CHARGED TO PAID-IN CAPITAL                              -                   -                    -
------------------------------------------------------------------------------------------------------------------------------------
DISTRIBUTIONS TO COMMON SHAREHOLDERS
   From and in excess of net investment income                                       (0.64)              (0.14)               (1.60)
   Return of capital                                                                     -               (1.46)                   -
------------------------------------------------------------------------------------------------------------------------------------
      Total distributions to common shareholders                                     (0.64)              (1.60)               (1.60)
------------------------------------------------------------------------------------------------------------------------------------
NET ASSET VALUE, END OF PERIOD                                                   $    9.35           $   10.24             $  17.79
====================================================================================================================================
MARKET VALUE, END OF PERIOD                                                      $    7.66           $    7.98             $  15.33
====================================================================================================================================
TOTAL INVESTMENT RETURN (c)
   Net asset value                                                                   -2.20%             -35.09%                2.54%
   Market value                                                                       4.25%             -39.88%               -8.45%

RATIOS AND SUPPLEMENTAL DATA
Net assets, end of period (thousands)                                            $ 177,783           $ 194,666             $338,072
Ratios to average net assets, including dividend expense on
securities sold short:
Total expense ratio                                                                   2.74%(d)            2.26%                2.81%
   Operating expense ratio                                                            1.82%(d)            1.41%                1.50%
   Dividends paid on securities sold short                                            0.92%(d)            0.85%                1.31%
Net investment income (loss) ratio                                                    0.47%(d)            0.36%               -0.55%
Portfolio turnover                                                                     139%                223%                 323%



                                                                                                           FOR THE PERIOD
                                                                                             FOR THE     AUGUST 25, 2005*
PER SHARE OPERATING PERFORMANCE                                                           YEAR ENDED              THROUGH
FOR A COMMON SHARE OUTSTANDING THROUGHOUT THE PERIOD                               DECEMBER 31, 2006    DECEMBER 31, 2005
=============================================================================================================================
                                                                                                          
NET ASSET VALUE, BEGINNING OF PERIOD                                                       $   18.80            $   19.10 (a)
-----------------------------------------------------------------------------------------------------------------------------
INCOME FROM INVESTMENT OPERATIONS
   Net investment income (loss)(b)                                                              0.07                 0.04
   Net realized and unrealized gain (loss) on investments, futures, options,
      securities sold short, forwards and foreign currency                                      1.62                 0.10
-----------------------------------------------------------------------------------------------------------------------------
      Total from investment operations                                                          1.69                 0.14
-----------------------------------------------------------------------------------------------------------------------------
COMMON SHARES' OFFERING EXPENSES CHARGED TO PAID-IN CAPITAL                                        -                (0.04)
-----------------------------------------------------------------------------------------------------------------------------
DISTRIBUTIONS TO COMMON SHAREHOLDERS
   From and in excess of net investment income                                                 (1.60)               (0.40)
   Return of capital                                                                               -                    -
-----------------------------------------------------------------------------------------------------------------------------
      Total distributions to common shareholders                                               (1.60)               (0.40)
-----------------------------------------------------------------------------------------------------------------------------
NET ASSET VALUE, END OF PERIOD                                                             $   18.89            $   18.80
=============================================================================================================================
MARKET VALUE, END OF PERIOD                                                                $   18.33            $   16.47
=============================================================================================================================
TOTAL INVESTMENT RETURN (c)
   Net asset value                                                                              9.36%                0.52%
   Market value                                                                                21.70%              -15.76%

RATIOS AND SUPPLEMENTAL DATA
Net assets, end of period (thousands)                                                      $ 359,036            $ 357,292
Ratios to average net assets, including dividend expense on
securities sold short:
Total expense ratio                                                                             2.00%                1.58%(d)(e)
   Operating expense ratio                                                                      1.52%                1.34%(d)
   Dividends paid on securities sold short                                                      0.48%                0.24%(d)(e)
Net investment income (loss) ratio                                                              0.39%                0.75%(d)(e)
Portfolio turnover                                                                               248%                  60%


*    Commencement of investment operations.

(a)  Before deduction of offering expenses charged to capital.

(b)  Based on average shares outstanding during the period.

(c)  Total investment return is calculated assuming a purchase of a common share
     at the beginning of the period and a sale on the last day of the period
     reported either at net asset value ("NAV") or market price per share.
     Dividends and distributions are assumed to be reinvested at NAV for NAV
     returns or the prices obtained under the Fund's Dividend Reinvestment Plan
     for market value returns. Total investment return does not reflect
     brokerage commissions. A return calculated for a period of less than one
     year is not annualized.

(d)  Annualized.

(e)  The expense ratio includes dividend payments made on securities sold short.
     During the approximate four month period from August 25, 2005 through
     December 31, 2005, nine securities sold short made two quarterly payments.
     The annualized ratios noted above have been adjusted such that these
     securities would only reflect the equivalent of four quarterly dividends
     per security. Had this adjustment not been made, the expense ratio would
     have been 1.65% and the net investment income ratio would have been 0.68%.



See notes to financial statements.

                                          Semiannual Report | June 30, 2009 | 19



OLA | Old Mutual/Claymore Long-Short Fund

Notes to FINANCIAL STATEMENTS | JUNE 30, 2009 (unaudited)


Note 1 - ORGANIZATION:
Old Mutual/Claymore Long-Short Fund (the "Fund") was organized as a
Massachusetts business trust on December 3, 2004. The Fund is registered as a
diversified, closed-end management investment company under the Investment
Company Act of 1940, as amended (the "1940 Act").

The Fund's primary investment objective is to provide a high level of current
income and current gains. The Fund's secondary investment objective is to
provide long-term capital appreciation. The Fund seeks to achieve its investment
objective by investing in a diversified portfolio of equity securities and by
selling securities short in the S&P 500 Index that it believes will underperform
relative to the average stock in the S&P 500. The Fund will also write (sell)
call options on equity indices and, to a lesser extent, on individual securities
held in the Fund's portfolio. The Fund may also employ a variety of other
strategies involving futures and forward contracts and other derivative
instruments in an attempt to enhance the Fund's investment returns. There can be
no assurance that the Fund's investment objective will be achieved.

Note 2 - ACCOUNTING POLICIES:
The preparation of the financial statements in accordance with U.S. generally
accepted accounting principles requires management to make estimates and
assumptions that affect the reported amounts and disclosures in the financial
statements. Actual results could differ from these estimates.

The following is a summary of significant accounting policies followed by the
Fund.

(a) VALUATION OF INVESTMENTS AND DERIVATIVES
Equity securities listed on an exchange are valued at the last reported sale
price on the primary exchange on which they are traded. Equity securities for
which there are no transactions on a given day are valued at the mean of the
closing bid and asked prices. Securities traded on NASDAQ are valued at the
NASDAQ Official Closing Price. Readily marketable securities listed on an
exchange are valued at the last reported sale price on the primary exchange or
in the principal over the counter ("OTC") market on which they are traded. Debt
securities are valued by independent pricing services or dealers using the mean
of the closing bid and asked prices for such securities or, if such prices are
not available, at prices for securities of comparable maturity, quality and
type. Equity index options are valued at the closing price on the primary
exchange on which they are traded. Futures and options on future contracts are
valued at the settlement price determined by the exchange on which they are
traded. Forward exchange currency contracts are valued daily at current exchange
rates. All other types of securities, including restricted securities, and
securities for which market quotations are not readily available, are valued as
determined in accordance with procedures established in good faith by the Board
of Trustees. Short-term securities having a remaining maturity of sixty days or
less at the time of purchase are valued at amortized cost, which approximates
market value.

For those securities whose quotations or prices are not available, the
valuations are determined in accordance with procedures established in good
faith by the Board of Trustees. Valuations in accordance with these procedures
are intended to reflect each security's (or asset's) "fair value". Such fair
value is the amount that the Fund might reasonably expect to receive for the
security (or asset) upon its current sale. Each such determination should be
based on a consideration of all relevant factors, which are likely to vary from
one pricing context to another. Examples of such factors may include, but are
not limited to: (i) the type of security, (ii) the initial cost of the security,
(iii) the existence of any contractual restrictions on the security's
disposition, (iv) the price and extent of public trading in similar securities
of the issuer or of comparable companies, (v) quotations or evaluated prices
from broker-dealers and/or pricing services, (vi) information obtained from the
issuer, analysts, and/or the appropriate stock exchange (for exchange traded
securities), (vii) an analysis of the company's financial statements, and (viii)
an evaluation of the forces that influence the issuer and the market(s) in which
the security is purchased and sold (e.g. the existence of pending merger
activity, public offerings or tender offers that might affect the value of the
security).

In September, 2006, the Financial Accounting Standards Board ("FASB") issued
Statement of Financial Accounting Standards No. 157, "Fair Valuation
Measurements" ("FAS 157"). The Fund adopted FAS 157 effective on January 1,
2008. This standard clarifies the definition of fair value for financial
reporting, establishes a framework for measuring fair value and requires
additional disclosures about the use of fair value measurements. FAS 157
establishes three different categories for valuations. Level 1 valuations are
those based upon quoted prices in active markets. Level 2 valuations are those
based upon quoted prices in inactive markets or based upon significant
observable inputs (e.g. yield curves; benchmark interest rates; indices). Level
3 valuations are those based upon unobservable inputs (e.g. discounted cash flow
analysis; non-market based methods used to determine fair valuation). In April
2009, the FASB issued FSP FAS 157-4, "Determining Fair Value When Volume and
Level of Activity for the Asset or Liability Have Significantly Decreased and
Identifying Transactions That Are Not Orderly" (FSP 157-4). FSP 157-4 provides
guidance on how to determine the fair value of assets and liabilities when the
volume and level of activity for the asset/liability has significantly
decreased. The Fund adopted FSP 157-4 effective on June 30, 2009. The following
table represents the Fund's investments carried on the Statement of Assets and
Liabilities by caption and by level within the fair value hierarchy as of June
30, 2009:


VALUATIONS (IN $000'S)
DESCRIPTION                   LEVEL 1      LEVEL 2        LEVEL 3        TOTAL
===============================================================================
Assets:
Common stocks
 Consumer Discretionary     $  19,611      $     -        $     -     $ 19,611
 Consumer Staples              21,533            -              -       21,533
 Energy                        26,794            -              -       26,794
 Financials                    29,542            -              -       29,542
 Health Care                   29,178            -              -       29,178
 Industrials                   18,933            -              -       18,933
 Information Technology        44,232            -              -       44,232
 Materials                      5,507            -              -        5,507
 Telecommunications             7,090            -              -        7,090
 Utilities                      6,182            -              -        6,182
Money Market Funds              5,776            -              -        5,776
U.S. Government Securities          -       13,519              -       13,519
Derivatives                         -        3,015*             -        3,015
-------------------------------------------------------------------------------
Total                        $214,378      $16,534        $     -     $230,912
===============================================================================

*    Reflects cumulative appreciation/depreciation of futures contracts as
     presented in the Notes to Financial Statements. The variation margin as of
     June 30, 2009 is reflected on the Statement of Assets and Liabilities.

20 | Semiannual Report | June 30, 2009



OLA | Old Mutual/Claymore Long-Short Fund | NOTES TO FINANCIAL STATEMENTS
(unaudited) continued

VALUATIONS AT JUNE 30, 2009
DESCRIPTION                   LEVEL 1      LEVEL 2        LEVEL 3        TOTAL
===============================================================================
(VALUE IN $000S)
Liabilities:
Common stocks
 Consumer Discretionary       $ 6,841     $      -       $      -     $  6,841
 Consumer Staples               2,411            -              -        2,411
 Energy                         5,137            -              -        5,137
 Financials                    12,620            -              -       12,620
 Health Care                    7,281            -              -        7,281
 Industrials                    3,519            -              -        3,519
 Information Technology         9,707            -              -        9,707
 Materials                        956            -              -          956
 Telecommunications             1,189            -              -        1,189
 Utilities                        301            -              -          301
Derivatives                     4,580        1,724*             -        6,304
-------------------------------------------------------------------------------
Total                         $54,542     $  1,724       $      -     $ 56,266
===============================================================================

(b) INVESTMENT TRANSACTIONS AND INVESTMENT INCOME
Investment transactions are accounted for on the trade date. Realized gains and
losses on investments are determined on the identified cost basis. Dividend
income is recorded net of applicable withholding taxes on the ex-dividend date
and interest income is recorded on an accrual basis. Discounts or premiums on
debt securities purchased are accreted or amortized to interest income over the
lives of the respective securities using the effective interest method.

(c) SECURITIES SOLD SHORT
The Fund may sell securities short. A short sale is a transaction in which the
Fund sells securities it does not own, but rather has borrowed, in anticipation
of a decline in the market price of the securities. The Fund is obligated to
replace the borrowed securities at their market price at the time of
replacement. The Fund's obligation to replace the securities borrowed in
connection with a short sale will be fully secured by collateral held in a
segregated account at the custodian. Short sales by the Fund involve certain
risks and special considerations. Possible losses from short sales differ from
losses that could be incurred from a purchase of a security because losses from
a short sale may be unlimited, whereas losses from purchases cannot exceed the
total amount invested.

Short equity securities listed on an exchange are valued at the last reported
sale price on the primary exchange on which they are traded. Short equity
securities for which there are no transactions on a given day are valued at the
mean of the closing bid and asked prices. Short equity securities traded on
NASDAQ are valued at the NASDAQ Official Closing Price. Readily marketable short
equity securities listed on an exchange are valued at the last reported sale
price on the primary exchange or in the principal over the counter ("OTC")
market on which they are traded.

(d) CURRENCY TRANSLATION
Assets and liabilities denominated in foreign currencies are translated into
U.S. dollars at the mean of the bid and asked price of respective exchange rates
on the last day of the period. Purchases and sales of investments denominated in
foreign currencies are translated at the exchange rate on the date of the
transaction.

Foreign exchange gain or loss resulting from holding of a foreign currency,
expiration of a currency exchange contract, difference in exchange rates between
the trade date and settlement date of an investment purchased or sold, and the
difference between dividends actually received compared to the amount shown in a
Fund's accounting records on the date of receipt are included as net realized
gains or losses on foreign currency forwards and currency transactions in the
Fund's Statement of Operations.

Foreign exchange gain or loss on assets and liabilities, other than investments,
are included in unrealized appreciation (depreciation) on foreign currency
translations.

(e) DISTRIBUTIONS TO SHAREHOLDERS
The Fund declares and pays quarterly dividends to common shareholders.
Distributions to shareholders are recorded on the ex-dividend date. The amount
and timing of distributions are determined in accordance with federal income tax
regulations, which may differ from U.S. generally accepted accounting
principles. These dividends consist of investment company taxable income, which
generally includes qualified dividend income, ordinary income, short-term
capital gains and premiums received on certain written options. Realized
short-term capital gains and premiums received on certain options are considered
ordinary income for tax purposes and will be reclassified at the Fund's fiscal
year end on the Fund's Statement of Assets and Liabilities from accumulated net
realized loss to accumulated net investment loss. Any net realized long-term
capital gains will be distributed annually to common shareholders. It is likely
that a substantial portion of the distributions paid during the calendar year
will ultimately be classified as return of capital for federal income tax
purposes.

(f) SUBSEQUENT EVENTS
Effective June 30, 2009, the Fund adopted Statement of Financial Accounting
Standards No. 165 ("SFAS No. 165"), "Subsequent Events". SFAS No. 165 requires
an entity to recognize in the financial statements the effects of all subsequent
events that provide additional evidence about conditions that existed at the
date of the balance sheet. SFAS No. 165 is intended to establish general
standards of accounting and for disclosure of events that occur after the
balance sheet date but before the financial statements are issued or are
available to be issued. The Fund has performed an evaluation of subsequent
events through August 24, 2009, which is the date the financial statements were
issued.

Note 3 - INVESTMENT ADVISORY AGREEMENT, SUB-ADVISORY AGREEMENT
         AND OTHER AGREEMENTS:

Pursuant to an Investment Advisory Agreement (the "Agreement") between the Fund
and Claymore Advisors, LLC (the "Adviser"), the Adviser will furnish offices,
necessary facilities and equipment, oversee the activities of Analytic
Investors, LLC. ("Analytic"or the "Sub-Adviser"), provide personnel including
certain officers required for its administrative management and pay the
compensation of all officers and trustees of the Fund who are its affiliates. As
compensation for these services, the Fund will pay the Adviser an annual fee,
payable monthly, in an amount equal to 1.00% of the Fund's average daily total
net assets.

Pursuant to a Sub-Advisory Agreement (the "Sub-Advisory Agreement") between the
Fund, the Adviser and the Sub-Adviser, the Sub-Adviser under the supervision of
the Fund's Board of Trustees and the Adviser, provides a continuous investment
program for the Fund's portfolio; provides investment research, makes and
executes recommendations for the purchase and sale of securities; and provides
certain facilities and personnel, including certain officers required for its
administrative management and pays the compensation of all officers and trustees
of the Fund who are its affiliates. As compensation for its services, the
Adviser pays the Sub-Adviser a fee, payable monthly, in an annual amount equal
to 0.50% of the Fund's average daily total net assets. Analytic is an affiliate
of Old Mutual (US) Holdings, Inc.


                                          Semiannual Report | June 30, 2009 | 21



OLA | Old Mutual/Claymore Long-Short Fund | NOTES TO FINANCIAL STATEMENTS
(unaudited) continued

The Adviser provides Fund Administration services to the Fund. For its services,
the Adviser receives a fund administration fee payable monthly at the annual
rate set forth below as a percentage of the average daily total net assets of
the Fund:

NET ASSETS                                                                  RATE
================================================================================
First $200,000,000                                                       0.0275%
Next $300,000,000                                                        0.0200%
Next $500,000,000                                                        0.0150%
Over $1,000,000,000                                                      0.0100%

The Bank of New York Mellon ("BNY") acts as the Fund's custodian, accounting
agent, and transfer agent. As custodian, BNY is responsible for the custody of
the Fund's assets. As accounting agent, BNY is responsible for maintaining the
books and records of the Fund's securities and cash. As transfer agent, BNY is
responsible for performing transfer agency services for the Fund.

Certain officers and trustees of the Fund are also officers and directors of the
Adviser or the Sub-Adviser. The Fund does not compensate its officers or
trustees who are officers of the aforementioned firms.

Note 4 - FEDERAL INCOME TAXES:
The Fund intends to comply with the requirements of Subchapter M of the Internal
Revenue Code of 1986, as amended, applicable to regulated investment companies.
Accordingly, no provision for U.S. federal income taxes is required. In
addition, by distributing substantially all of its ordinary income and long-term
capital gains, if any, during each calendar year, the Fund intends not to be
subject to U.S. federal excise tax.

Capital losses and foreign currency transactions incurred after October 31
("post-October" losses) within the taxable year are deemed to arise on the first
business day of the Fund's next taxable year. The Fund incurred and elected to
defer capital losses and foreign currency related losses from 2008 in the amount
of $10,379,228 and $1,619,801, respectively.

Information on the tax components of investments, excluding short sales
transactions and excluding written options, and net assets as of June 30, 2009
is as follows:

                                                                        NET TAX
     COST OF                                         NET TAX         UNREALIZED
 INVESTMENTS      GROSS TAX       GROSS TAX       UNREALIZED    APPRECIATION ON
     FOR TAX     UNREALIZED      UNREALIZED  DEPRECIATION ON    DERIVATIVES AND
    PURPOSES   APPRECIATION    DEPRECIATION      INVESTMENTS   FOREIGN CURRENCY
================================================================================
$264,817,178     $3,374,684   ($40,295,007)    ($36,920,323)           $638,288

Information on the tax components of securities sold short as of June 30, 2009
is as follows:

                                                                        NET TAX
 PROCEEDS FROM                                                       UNREALIZED
    SECURITIES          GROSS TAX            GROSS TAX             DEPRECIATION
SOLD SHORT FOR         UNREALIZED           UNREALIZED            ON SECURITIES
  TAX PURPOSES       APPRECIATION         DEPRECIATION               SOLD SHORT
================================================================================
   $43,436,051         $1,061,716         ($7,587,243)             ($6,525,527)

Tax components of the following balances as of December 31, 2008 are as follows:

                                                              DECEMBER 31, 2008
================================================================================
Accumulated Net Investment Loss                                    ($1,619,801)
Accumulated Capital and Other Losses                              ($37,913,175)


For the year ended December 31, 2008, the tax character of distributions paid to
shareholders as reflected in the Statement of Changes in Net Assets, was as
follows:

DISTRIBUTIONS PAID FROM:                                                   2008
================================================================================
Ordinary Income                                                  $    2,749,600
Capital Gain                                                              5,713
Return of Capital                                                    27,653,071
--------------------------------------------------------------------------------
                                                                 $   30,408,384
--------------------------------------------------------------------------------

At December 31, 2008, for federal income tax purposes, the Fund had a capital
loss carryforward of $27,533,947 available to offset possible future capital
gains. The capital loss carryforward is set to expire December 31, 2016.

Effective January 1, 2008, the Fund adopted the provisions of FASB
Interpretation No. 48 ("FIN 48") Accounting for Uncertainty in Income Taxes. FIN
48 sets forth a minimum threshold for financial statement recognition of the
benefit of a tax position taken or expected to be taken in a tax return. The
implication of FIN 48 did not result in any unrecognized tax benefits in the
accompanying financial statements.

FIN 48 requires the Fund to analyze all open tax years. Open tax years are those
years that are open for examination by the relevant income taxing authority.
Open federal and state income tax years include the tax years ended 2005, 2006,
2007 and 2008. The Fund has no examinations in progress.

Note 5 - INVESTMENT TRANSACTIONS:
For the six months ended June 30, 2009, purchases and sales of investments,
excluding written options with maturities of less than one year and short-term
securities, were $320,945,947 and $332,317,816, respectively.

Note 6 - DERIVATIVES:
In March 2008, the FASB issued SFAS No.161, "Disclosures about Derivative
Instruments and Hedging Activities." This standard is intended to enhance
financial statement disclosures for derivative instruments and hedging
activities and enable investors to understand: a) how and why a fund uses
derivative instruments, b) how derivative instruments and related hedge fund
items are accounted for, and c) how derivative instruments and related hedge
items affect a fund's financial position, results of operations, and cash flows.
The Fund adopted SFAS No. 161 effective January 1, 2009.

The Fund may engage in asset allocation strategies by purchasing or selling
futures contracts on U.S. and foreign securities, indices and other assets. A
futures contract provides for the future sale by one party and purchase by
another party of a specified quantity of the security or other financial
instrument at a specified price and time. A futures contract on an index is an
agreement in which two parties agree to take or make delivery of an amount of
cash equal to the difference between the value of the index at the close of the
last trading day of the contract and the price at which the index contract was
originally written. Upon entering into futures contracts, the Fund maintains an
amount of cash or liquid securities with a value equal to a percentage of the
contract amount with either a futures commission merchant pursuant to rules and
regulations promulgated under the 1940 Act, as amended, or with its custodian in
an account in the broker's name. This amount is known as initial margin. During
the period the futures contract is open, payments are received from or made to
the broker based upon changes in the value of the contract (the variation
margin). The risk of loss associated with a futures contract is in excess of the
variation margin reflected on the Statement of Assets and Liabilities. The Fund
may use futures contracts in an attempt to enhance the Fund's investment
returns, as an efficient way to gain broad market exposure with reduced transac-


22 | Semiannual Report | June 30, 2009



OLA | Old Mutual/Claymore Long-Short Fund | NOTES TO FINANCIAL STATEMENTS
(unaudited) continued

tion costs and/or to hedge against market and other risks in the Fund's
portfolio. There are a number of risks associated with the use of futures
contracts. A purchase or sale of a futures contract may result in losses in
excess of the amount invested in the futures contract. If futures are used for
hedging, there can be no guarantee that there will be a correlation between
price movements in the hedging vehicle and in the Fund's portfolio securities
being hedged. During the period covered by this report, Analytic also pursued a
global asset allocation strategy which sought to generate incremental investment
returns with a low correlation to the rest of the Fund's portfolio by taking
long and short positions in global equity and fixed-income markets. Given the
unprecedented volatility in the market and performance of the global asset
allocation, the Fund announced on July 20, 2009 that it is suspending its use of
this component of its overall investment strategy. The other elements of the
strategy remain unchanged.

The Fund will opportunistically employ an option strategy in an attempt to
generate gains from option premiums, enhance distributions payable to the Fund's
shareholders and reduce overall portfolio risk. The Fund intends to pursue its
options strategy primarily by writing call options on equity indices. As the
writer (seller) of an equity index call option, the Fund would receive cash (the
premium) from the purchaser of the option, and the purchaser would have the
right to receive from the Fund any appreciation in the cash value of the index
over the strike price upon exercise. If the purchaser exercises the index option
sold by the Fund, the Fund would pay the purchaser the difference between the
cash value of the index and the strike price. In effect, the Fund sells the
potential appreciation in the value of the index above the strike price in
exchange for the premium.

The Fund may enter into forward exchange currency contracts in order to hedge
its exposure to changes in foreign currency exchange rates on its foreign
portfolio holdings, to hedge certain firm purchases and sales commitments
denominated in foreign currencies and for investment purposes. A forward
exchange currency contract is a commitment to purchase or sell a foreign
currency on a future date at a negotiated forward rate. The gain or loss arising
from the difference between the original contracts and the closing of such
contracts are included in net realized gain or loss on foreign currency forwards
and currency transactions on the Statement of Operations. Fluctuations in the
value of open forward exchange currency contracts are recorded for financial
reporting purposes as unrealized appreciation and depreciation on foreign
currency forwards and currency translation on the Statement of Operations. The
Fund's custodian will place and maintain cash not available for investment or
other liquid assets in a separate account of the Fund having a value at least
equal to the aggregate amount of the Fund's commitments under forward exchange
currency contracts entered into with respect to position hedges. Risks may arise
from the potential inability of a counterparty to meet the terms of a contract
and from unanticipated movements in the value of a foreign currency relative to
the U.S. dollar. The face or contract amount, in U.S. dollars, reflects the
total exposure the Fund has in that particular currency contract.

At June 30, 2009, the following futures contracts were outstanding:



                                                                                          UNREALIZED
                                                                       NUMBER OF        APPRECIATION
LONG CONTRACTS                                                         CONTRACTS      (DEPRECIATION)
-----------------------------------------------------------------------------------------------------
                                                                                
Australian Dollar - September 2009
  (Current notional value of $80,290 per contract)                           365       $     123,740
British Pound - September 2009
  (Current notional value of $102,894 per contract)                           76              43,446
China Hang Seng Index - July 2009
  (Current notional value of 921,000 Hong Kong dollars per contract)           2               3,893
France CAC 40 10 Euros - July 2009
  (Current notional value of 31,360 Euro per contract)                       218            (251,275)
Germany DAX Index - September 2009
  (Current notional value of 120,488 Euro per contract)                        7             (19,333)
Japanese Yen - September 2009
  (Current notional value of $129,850 per contract)                           48             107,158
Japan TOPIX Index - September 2009
  (Current notional value of 9,245,000 Japanese Yen per contract)             92              61,387
Spain IBEX 35 Index - July 2009
  (Current notional value of 97,170 Euro per contract)                       106             422,350
Swedish Krona - September 2009
  (Current notional value of $259,420 per contract)                          120            (232,380)
United Kingdom FTSE 100 Index - September 2009
  (Current notional value of 42,180 Pound Sterling per contract)              93            (115,846)
U.S. CBOE Volatility Index - July 2009
  (Current notional value of $28,050 per contract)                           160            (407,200)
U.S. S&P 500 EMINI - September 2009
  (Current notional value of $45,775 per contract)                           229              (4,785)
-----------------------------------------------------------------------------------------------------
                                                                           1,516      $     (268,845)
-----------------------------------------------------------------------------------------------------

                                                                                          UNREALIZED
                                                                       NUMBER OF        APPRECIATION
SHORT CONTRACTS                                                        CONTRACTS      (DEPRECIATION)
-----------------------------------------------------------------------------------------------------
Amsterdam Exchanges Index - July 2009
  (Current notional value of 50,890 Euro per contract)                        77      $       86,215
Australia SPI 200 Index - September 2009
  (Current notional value of 97,525 Australian dollars per contract)         183             225,471
Canada S&P/TSE 60 Index - September 2009
  (Current notional value of 125,420 Canadian dollars per contract)          121             351,930
Canadian Dollar - September 2009
  (Current notional value of $86,100 per contract)                           353           1,481,758
Euro FX - September 2009
  (Current notional value of $175,500 per contract)                          183             (46,482)
Italy FTSE/MIB Index - September 2009
  (Current notional value of 95,440 Euro per contract)                        32             107,198
New Zealand Dollar - September 2009
  (Current notional value of $64,310 per contract)                           300            (517,200)
Sweden OMXS30 - July 2009
  (Current notional value of 79,500 Swedish Krona per contract)              942            (129,581)
-----------------------------------------------------------------------------------------------------
                                                                           2,191      $    1,559,309
-----------------------------------------------------------------------------------------------------
                                                                           3,707      $    1,290,464
=====================================================================================================


                                          Semiannual Report | June 30, 2009 | 23



OLA | Old Mutual/Claymore Long-Short Fund | NOTES TO FINANCIAL STATEMENTS
(unaudited) continued

The following table presents the types of derivatives in the Fund by location as
presented on the Statement of Assets Liabilities as of June 30, 2009.



STATEMENT OF ASSET AND LIABILITY PRESENTATION OF FAIR VALUES OF DERIVATIVE
INSTRUMENTS:
-----------------------------------------------------------------------------------
(AMOUNT IN THOUSANDS)

AS OF JUNE 30, 2009              ASSET DERIVATIVES          LIABILITY DERIVATIVES
-----------------------------------------------------------------------------------
                                                                 
DERIVATIVES NOT ACCOUNTED
FOR AS HEDGING INSTRUMENTS   BALANCE SHEET       FAIR      BALANCE SHEET      FAIR
UNDER STATEMENT 133          LOCATION           VALUE      LOCATION          VALUE
-----------------------------------------------------------------------------------
Foreign exchange             Variation margin              Variation margin
contracts                    on futures        $1,756*     on futures         $796*
                             Variation margin              Variation margin
Equity contracts             on futures         1,258*     on futures          928*
                             Options written,
Equity contracts             at value               5      N/A                   -
-----------------------------------------------------------------------------------
Total                                          $3,019                       $1,724
===================================================================================


*    Reflects cumulative appreciation/depreciation of futures contracts as
     presented in the Notes to Financial Statements. The variation margin as of
     June 30, 2009 is reflected on the Statement of Assets and Liabilities.

The following table presents the effect of Derivatives Instruments on the
Statement of Operations for the six months ended June 30, 2009.

EFFECT OF DERIVATIVE INSTRUMENTS ON THE STATEMENT OF OPERATIONS FOR THE PERIOD
ENDED JUNE 30, 2009:
--------------------------------------------------------------------------------
(AMOUNT IN THOUSANDS)
                  AMOUNT OF REALIZED GAIN (LOSS) ON DERIVATIVES
--------------------------------------------------------------------------------
DERIVATIVES NOT ACCOUNTED FOR AS
HEDGING INSTRUMENTS UNDER                              FOREIGN CURRENCY
STATEMENT 133                 FUTURES      OPTIONS     FORWARDS           TOTAL
--------------------------------------------------------------------------------
Foreign exchange contracts    $   511   $        -     $    1,238      $  1,749
Equity contracts                  864            -              -           864
Equity contracts                    -       (5,236)             -        (5,236)
--------------------------------------------------------------------------------
Total                         $ 1,375   $   (5,236)    $    1,238      $ (2,623)
================================================================================

CHANGE IN UNREALIZED APPRECIATION (DEPRECIATION) ON DERIVATIVES
--------------------------------------------------------------------------------
DERIVATIVES NOT ACCOUNTED FOR AS
HEDGING INSTRUMENTS UNDER                              FOREIGN CURRENCY
STATEMENT 133                 FUTURES      OPTIONS     FORWARDS           TOTAL
--------------------------------------------------------------------------------
Foreign exchange contracts    $   960   $        -     $   (1,220)      $  (260)
Equity contracts                1,025            -              -         1,025
Interest rate contracts        (2,616)           -              -        (2,616)
Equity contracts                    -       (1,729)             -        (1,729)
--------------------------------------------------------------------------------
Total                         $  (631)  $   (1,729)    $   (1,220)      $(3,580)
================================================================================

Transactions in written call option contracts during the six months ended June
30, 2009 were as follows:

                                                      NUMBER OF        PREMIUMS
                                                      CONTRACTS        RECEIVED
--------------------------------------------------------------------------------
Options outstanding, beginning of year                    4,737    $  5,563,001
--------------------------------------------------------------------------------
Options written, during the period                      169,522      99,687,525
Options expired, during the period                      (24,222)    (10,024,213)
Options closed, during the period                      (140,216)    (90,642,161)
--------------------------------------------------------------------------------
Options outstanding, end of period                        9,821    $  4,584,152
================================================================================

Transactions in futures contracts during the six months ended June 30, 2009 were
as follows:

                                                                      NUMBER OF
                                                                      CONTRACTS
--------------------------------------------------------------------------------
Futures outstanding, beginning of year                                    3,787
--------------------------------------------------------------------------------
Futures opened                                                           25,555
Futures closed                                                          (25,635)
--------------------------------------------------------------------------------
Futures outstanding, end of period                                        3,707
================================================================================

NOTE 7 - CAPITAL:

COMMON SHARES
The Fund has an unlimited amount of common shares, $0.01 par value, authorized
and 19,005,240 issued and outstanding.

There were no transactions in common shares during the six months ended June 30,
2009 nor the year ended December 31, 2008.

NOTE 8 - INDEMNIFICATIONS:
In the normal course of business, the Fund enters into contracts that contain a
variety of representations, which provide general indemnifications. The Fund's
maximum exposure under these arrangements is unknown, as this would require
future claims that may be made against the Fund that have not yet occurred.
However, the Fund expects the risk of loss to be remote.

Note 9 - SUBSEQUENT EVENTS:
On July 17, 2009, Claymore Group Inc., the parent of the Adviser, entered into
an Agreement and Plan of Merger between and among Claymore Group Inc., Claymore
Holdings, LLC and GuggClay Acquisition, Inc., (with the latter two entities
being wholly-owned, indirect subsidiaries of Guggenheim Partners, LLC
("Guggenheim")) whereby GuggClay Acquisition, Inc. will merge into Claymore
Group Inc. which will be the surviving entity. The parties intend that the
completed merger will result in a change-of-control whereby Claymore Group Inc.
and its subsidiaries, including the Adviser, will become indirect, wholly-owned
subsidiaries of Guggenheim. The transaction is not expected to affect the daily
operations of the Fund or the investment management activities of the Adviser.

Under the 1940 Act, consummation of this transaction will result in the
automatic termination of the Advisory Agreement. Accordingly, prior to such
consummation, the Fund expects to enter into a new investment advisory agreement
with the Adviser, to become effective upon the consummation of the transaction.
This new investment advisory agreement will be subject to the initial approval
of the Board of Trustees and subsequent approval by the Fund's shareholders.


24 | Semiannual Report | June 30, 2009



OLA | Old Mutual/Claymore Long-Short Fund

Supplemental  INFORMATION | (unaudited)


FEDERAL INCOME TAX INFORMATION
In January 2010, you will be advised on IRS Form 1099 DIV or substitute 1099 DIV
as to the federal tax status of the distributions received by you in the
calendar year 2009.


RESULTS OF SHAREHOLDER VOTES
The Annual Meeting of Shareholders of the Fund was held on July 20, 2009. Common
shareholders voted on the election of Trustees.

With regard to the election of the following Class I Trustees by common
shareholders of the Fund:

                                 # OF SHARES                        # OF SHARES
                                    IN FAVOR                           WITHHELD
================================================================================
Matthew J. Appelstein             16,158,316                          1,106,127
Randall C. Barnes                 16,208,084                          1,056,359

The other Trustees of the Fund whose terms did not expire in 2009 are Steven D.
Cosler, Robert M. Hamje, L. Kent Moore, Ronald A. Nyberg, Ronald E. Toupin, Jr.
and Nicholas Dalmaso.




TRUSTEES
The Trustees of the Old Mutual/Claymore Long-Short Fund and their principal
occupations during the past five years:

                                                                                    NUMBER OF
NAME, ADDRESS,* YEAR OF       TERM OF OFFICE**   PRINCIPAL OCCUPATIONS DURING       PORTFOLIOS IN THE
BIRTH AND POSITION(S)         AND LENGTH OF      THE PAST FIVE YEARS AND            FUND COMPLEX***         OTHER DIRECTORSHIPS
HELD WITH REGISTRANT          TIME SERVED        OTHER AFFILIATIONS                 OVERSEEN BY TRUSTEE     HELD BY TRUSTEE
===================================================================================================================================
INDEPENDENT TRUSTEES:
===================================================================================================================================
                                                                                                
Randall C. Barnes             Since 2005         Private Investor (2001-present).          43               None.
Year of Birth: 1951                              Formerly, Senior Vice President
Trustee                                          & Treasurer, PepsiCo. Inc.
                                                 (1993-1997), President, Pizza Hut
                                                 International (1991-1993) and
                                                 Senior Vice President, Strategic
                                                 Planning and New Business Development
                                                 (1987-1990) of PepsiCo, Inc.
                                                 (1987-1997).
-----------------------------------------------------------------------------------------------------------------------------------
Steven D. Cosler              Since 2005         Formerly, President, Chief Executive      2                Director, SXC Health
Year of Birth: 1955                              Officer and Director of Priority                           Solutions, Corp.
Trustee                                          Healthcare Corp. (2002-2005).
                                                 Formerly, President and Chief
                                                 Operating Officer of Priority
                                                 Healthcare Corp. (2001-2002).
                                                 Formerly, Executive Vice President
                                                 and Chief Operating Officer of
                                                 Priority Healthcare Corp.
                                                 (2000-2001).
-----------------------------------------------------------------------------------------------------------------------------------
Robert M. Hamje               Since 2005         Formerly, President and Chief             2                Trustee, Old Mutual
Year of Birth: 1942                              Investment Officer of TRW                                  Advisor Mutual Funds.
Trustee                                          Investment Management Co.
                                                 (1990-2003).
-----------------------------------------------------------------------------------------------------------------------------------
L. Kent Moore                 Since 2005         Partner at WilSource Enterprise           2                Trustee, Old Mutual
Year of Birth: 1955                              (December 2005-Present).                                   Advisor Mutual Funds.
Trustee                                          Previously, Managing Director
                                                 High Sierra Energy L.P.,
                                                 (2004-2005). Formerly, Portfolio
                                                 Manager and Vice President of
                                                 Janus Capital Corp. (2000-2002)
                                                 and Senior Analyst/Portfolio
                                                 Manager of Marsico Capital
                                                 Management (1997-1999).
-----------------------------------------------------------------------------------------------------------------------------------
Ronald A. Nyberg              Since 2005         Partner of Nyberg & Cassioppi,            46               None.
Year of Birth: 1953                              LLC, a law firm specializing in
Trustee                                          corporate law, estate planning
                                                 and business transactions
                                                 (2000-present). Formerly, Executive
                                                 Vice President, General Counsel and
                                                 Corporate Secretary of Van Kampen
                                                 Investments (1982-1999).
-----------------------------------------------------------------------------------------------------------------------------------
Ronald E. Toupin, Jr.         Since 2005         Retired. Formerly, Vice President,        43               None.
Year of Birth: 1958                              Manager and Portfolio Manager of
Trustee                                          Nuveen Asset Management
                                                 (1998-1999), Vice President of
                                                 Nuveen Investment Advisory Corp.
                                                 (1992-1999), Vice President and
                                                 Manager of Nuveen Unit Investment
                                                 Trusts (1991-1999), and Assistant
                                                 Vice President and Portfolio
                                                 Manager of Nuveen Unit Investment
                                                 Trusts (1988-1999), each of John
                                                 Nuveen & Co., Inc. (1982-1999).
-----------------------------------------------------------------------------------------------------------------------------------
INTERESTED TRUSTEES:
===================================================================================================================================
Matthew J. Appelstein+        Since 2005         Senior Vice President of Product          2                None.
Year of Birth: 1961                              Strategy and Retirement Solutions
Trustee                                          Planning, Director of Investment
                                                 Services, Old Mutual Asset Management
                                                 (2003-present). Formerly, Senior Vice
                                                 President of Consulting Relationships,
                                                 Fidelity Management Trust Co.
                                                 (1998-2003).
-----------------------------------------------------------------------------------------------------------------------------------
Nicholas Dalmaso++            Since 2005         Attorney. Formerly, Senior Managing       45               None.
Year of birth: 1965                              Director and Chief Administrative
Trustee                                          Officer (2007-2008) and General
                                                 Counsel (2001-2007)of Claymore
                                                 Advisors, LLC and Claymore
                                                 Securities, Inc. (2001-2008).
                                                 Formerly, Assistant General
                                                 Counsel, John Nuveen and Company,
                                                 Inc. (1999-2000). Former Vice
                                                 President and Associate General
                                                 Counsel of Van Kampen Investments,
                                                 Inc. (1992-1999).
-----------------------------------------------------------------------------------------------------------------------------------


*    Address for all Trustees unless otherwise noted: 2455 Corporate West Drive,
     Lisle, IL 60532

**   After a Trustee's initial term, each Trustee is expected to serve a
     three-year term concurrent with the class of Trustees for which he serves:

     -Messrs. Appelstein and Barnes, as Class I Trustees, are expected to stand
     for re-election at the Fund's 2012 annual meeting of shareholders.

     -Messrs. Cosler, Dalmaso and Hamje, as Class II Trustees, are expected to
     stand for re-election at the Fund's 2010 annual meeting of shareholders.

     -Messrs. Moore, Nyberg and Toupin, as Class III Trustees, are expected to
     stand for re-election at the Fund's 2011 annual meeting of shareholders.

***  The Claymore Fund Complex consists of U.S. registered investment companies
     advised or serviced by Claymore Advisors, LLC or Claymore Securities, Inc.
     The Claymore Fund Complex is overseen by multiple Boards of Trustees.

+    Mr. Appelstein is an "interested person" (as defined in Section 2(a)(19) of
     the 1940 Act) of the Fund because of his position as an officer of Old
     Mutual Asset Management, the parent company of the Fund's Sub-Adviser.

++   Mr. Dalmaso is an "interested person" (as defined in section 2(a)(19) of
     the 1940 Act) of the Fund because of his former position as an officer of,
     and his equity ownership in, the Fund's Investment Adviser and certain of
     its affiliates.

                                          Semiannual Report | June 30, 2009 | 25


OLA | Old Mutual/Claymore Long-Short Fund | SUPPLEMENTAL INFORMATION (unaudited)
continued




OFFICERS
The Officers of the Old Mutual/Claymore Long-Short Fund and their principal
occupations during the past five years:


NAME, ADDRESS*, YEAR OF BIRTH AND       TERM OF OFFICE** AND        PRINCIPAL OCCUPATIONS DURING THE PAST FIVE YEARS
POSITION(S) HELD WITH REGISTRANT        LENGTH OF TIME SERVED       AND OTHER AFFILIATIONS
====================================================================================================================================
OFFICERS:
====================================================================================================================================
                                                              
J. Thomas Futrell                       Since 2008                  Senior Managing Director and Chief Investment Officer of
Year of birth: 1955                                                 Claymore Advisors, LLC and Claymore Securities, Inc.
Chief Executive Officer                                             (2008-present). Chief Executive Officer  of certain other funds
                                                                    in the Fund Complex. Formerly, Managing Director of Research,
                                                                    Nuveen Asset Management (2000-2007).
------------------------------------------------------------------------------------------------------------------------------------
Kevin M. Robinson                       Since 2008                  Senior Managing Director and General Counsel of Claymore
Year of birth: 1959                                                 Advisors, LLC, Claymore Securities, Inc. and Claymore Group
Chief Legal Officer                                                 Inc. (2007-present). Chief Legal Officer of certain other funds
                                                                    in the Fund Complex. Formerly, Associate General Counsel and
                                                                    Assistant Corporate Secretary of NYSE Euronext, Inc.
                                                                    (2000-2007).
------------------------------------------------------------------------------------------------------------------------------------
Steven M. Hill                          Since 2005                  Senior Managing Director of Claymore Advisors, LLC and Claymore
Year of Birth: 1964                                                 Securities, Inc. (2005- present). Previously, Chief Financial
Chief Accounting Officer,                                           Officer of Claymore Group Inc. (2005-2006). Managing Director
Chief Financial Officer and Treasurer                               of Claymore Advisors, LLC and Claymore Securities, Inc.
                                                                    (2003-2005). Treasurer of Henderson Global Funds and Operations
                                                                    Manager for Henderson Global Investors (North America) Inc.
                                                                    (2002-2003); Managing Director, FrontPoint Partners LLC
                                                                    (2001-2002); Vice President, Nuveen Investments (1999-2001);
                                                                    Chief Financial Officer, Skyline Asset Management LP (1999);
                                                                    Vice President, Van Kampen Investments and Assistant Treasurer,
                                                                    Van Kampen mutual funds (1989-1999).
------------------------------------------------------------------------------------------------------------------------------------
Mark E. Mathiasen                       Since 2009                  Vice President, Assistant General Counsel of Claymore Group
Year of Birth: 1978                                                 Inc. (2007 to present). Secretary of certain funds in the Fund
Secretary                                                           Complex. Previously, Law Clerk for the Idaho State Courts
                                                                    (2003-2007).
------------------------------------------------------------------------------------------------------------------------------------
Bruce Saxon                             Since 2006                  Vice President-Fund Compliance Officer of Claymore Group Inc.
Year of Birth: 1957                                                 (Feb 2006-present). Previously, Chief Compliance
Chief Compliance Officer                                            Officer/Assistant Secretary of Harris Investment Management,
                                                                    Inc. (2003-2006). Director-Compliance of Harrisdirect LLC
                                                                    (1999-2003).
------------------------------------------------------------------------------------------------------------------------------------


*    Address for all Officers: 2455 Corporate West Drive, Lisle, IL 60532

**   Officers serve at the pleasure of the Board of Trustees and until his or
     her successor is appointed and qualified or until his or her earlier
     resignation or removal.

26 | Semiannual Report | June 30, 2009



OLA | Old Mutual/Claymore Long-Short Fund

Dividend Reinvestment PLAN |(unaudited)

Unless the registered owner of common shares elects to receive cash by
contacting the Bank of New York Mellon (the "Plan Administrator"), all dividends
declared on common shares of the Fund will be automatically reinvested by the
Plan Administrator for shareholders in the Fund's Dividend Reinvestment Plan
(the "Plan"), in additional common shares of the Fund. Participation in the Plan
is completely voluntary and may be terminated or resumed at any time without
penalty by notice if received and processed by the Plan Administrator prior to
the dividend record date; otherwise such termination or resumption will be
effective with respect to any subsequently declared dividend or other
distribution. Some brokers may automatically elect to receive cash on your
behalf and may re-invest that cash in additional common shares of the Fund for
you. If you wish for all dividends declared on your common shares of the Fund to
be automatically reinvested pursuant to the Plan, please contact your broker.

The Plan Administrator will open an account for each common shareholder under
the Plan in the same name in which such common shareholder's common shares are
registered. Whenever the Fund declares a dividend or other distribution
(together, a "Dividend") payable in cash, non-participants in the Plan will
receive cash and participants in the Plan will receive the equivalent in common
shares. The common shares will be acquired by the Plan Administrator for the
participants' accounts, depending upon the circumstances described below, either
(i) through receipt of additional unissued but authorized common shares from the
Fund ("Newly Issued Common Shares") or (ii) by purchase of outstanding common
shares on the open market ("Open-Market Purchases") on the New York Stock
Exchange or elsewhere. If, on the payment date for any Dividend, the closing
market price plus estimated brokerage commission per common share is equal to or
greater than the net asset value per common share, the Plan Administrator will
invest the Dividend amount in Newly Issued Common Shares on behalf of the
participants. The number of Newly Issued Common Shares to be credited to each
participant's account will be determined by dividing the dollar amount of the
Dividend by the net asset value per common share on the payment date; provided
that, if the net asset value is less than or equal to 95% of the closing market
value on the payment date, the dollar amount of the Dividend will be divided by
95% of the closing market price per common share on the payment date. If, on the
payment date for any Dividend, the net asset value per common share is greater
than the closing market value plus estimated brokerage commission, the Plan
Administrator will invest the Dividend amount in common shares acquired on
behalf of the participants in Open-Market Purchases.

If, before the Plan Administrator has completed its Open-Market Purchases, the
market price per common share exceeds the net asset value per common share, the
average per common share purchase price paid by the Plan Administrator may
exceed the net asset value of the common shares, resulting in the acquisition of
fewer common shares than if the Dividend had been paid in Newly Issued Common
Shares on the Dividend payment date. Because of the foregoing difficulty with
respect to Open-Market Purchases, the Plan provides that if the Plan
Administrator is unable to invest the full Dividend amount in Open-Market
Purchases during the purchase period or if the market discount shifts to a
market premium during the purchase period, the Plan Administrator may cease
making Open-Market Purchases and may invest the uninvested portion of the
Dividend amount in Newly Issued Common Shares at net asset value per common
share at the close of business on the Last Purchase Date provided that, if the
net asset value is less than or equal to 95% of the then current market price
per common share; the dollar amount of the Dividend will be divided by 95% of
the market price on the payment date.

The Plan Administrator maintains all shareholders' accounts in the Plan and
furnishes written confirmation of all transactions in the accounts, including
information needed by shareholders for tax records. Common shares in the account
of each Plan participant will be held by the Plan Administrator on behalf of the
Plan participant, and each shareholder proxy will include those shares purchased
or received pursuant to the Plan. The Plan Administrator will forward all proxy
solicitation materials to participants and vote proxies for shares held under
the Plan in accordance with the instruction of the participants.

There will be no brokerage charges with respect to common shares issued directly
by the Fund. However, each participant will pay a pro rata share of brokerage
commission incurred in connection with Open-Market Purchases. The automatic
reinvestment of Dividends will not relieve participants of any Federal, state or
local income tax that may be payable (or required to be withheld) on such
Dividends.

The Fund reserves the right to amend or terminate the Plan. There is no direct
service charge to participants with regard to purchases in the Plan; however,
the Fund reserves the right to amend the Plan to include a service charge
payable by the participants.

All correspondence or questions concerning the Plan should be directed to the
Plan Administrator, BNY Mellon Shareowner Services, PO Box 358015, Pittsburgh,
PA 15252-8015, Phone Number: (866) 488-3559.



                                          Semiannual Report | June 30, 2009 | 27



OLA | Old Mutual/Claymore Long-Short Fund

Board Considerations Regarding Investment
Advisory Agreement and Subadvisory Agreement CONTRACT RE-APPROVAL |

On January 20, 2009, the Board of Trustees (the "Board"), including those
trustees who are not interested persons as defined by the Investment Company Act
of 1940 (the "Independent Trustees") of the Old Mutual/Claymore Long-Short Fund
(the "Fund") met to consider the renewal of: (1) the investment advisory
agreement ("Investment Advisory Agreement") between the Fund and Claymore
Advisors, LLC ("Adviser") and (2) the subadvisory agreement (the "Subadvisory
Agreement") among the Adviser, the Fund and Analytic Investors LLC (the
"Subadviser"). (The Investment Advisory Agreement and the Subadvisory Agreement
are together referred to as the "Advisory Agreements.") As part of its review
process, the Nominating and Governance Committee of the Board (referred to as
the "Committee" and consisting solely of the Independent Trustees) was
represented by independent legal counsel. The Board reviewed materials received
from the Adviser, Subadviser and independent legal counsel.

In preparation for its review, the Committee communicated with independent legal
counsel regarding the nature of information to be provided, and independent
legal counsel, on behalf of the Committee, sent a formal request for
information. The Adviser and the Subadviser provided extensive information in
response to the request as well as to a follow-up request for supplemental
information. Among other information, the Adviser and the Subadviser provided
general information to assist the Committee in assessing the nature and quality
of services provided by the Adviser and the Subadviser and information comparing
the investment performance, advisory fee and total expenses of the Fund to other
funds, information about the profitability of the Advisory Agreements to the
Adviser and the Subadviser and the compliance program of each of the Adviser and
the Subadviser.

Based upon their review, the Committee and the Board concluded that it was in
the best interests of the Fund to renew each of the Advisory Agreements. In
reaching this conclusion for the Fund, no single factor was determinative in the
Board's analysis, but rather the Board considered a variety of factors.


INVESTMENT ADVISORY AGREEMENT
With respect to the nature, extent and quality of services currently provided by
the Adviser, the Board noted that the Adviser had delegated responsibility for
the investment and reinvestment of the Fund's assets to the Subadviser. The
Board considered the Adviser's responsibility to oversee the Subadviser and that
the Adviser has similar oversight responsibilities for other registered funds
for which it serves as investment adviser. The Board reviewed financial
information regarding the Adviser and its parent company and considered the
parent company's guaranty of the Adviser's obligations under the Investment
Advisory Agreement. The Board considered the experience and qualifications of
the personnel providing services to the Fund. Specifically, the Board noted the
ongoing oversight activities performed by the Adviser, including on-site
diligence visits and regular monitoring of compliance with policies and
procedures and with the Fund's investment parameters as described in its
prospectus and statement of additional information. The Board considered the
secondary market support services provided by the Adviser to the Fund and the
Adviser's collaboration with the Sub-Adviser in evaluating the Fund's
distribution rate.

The Board reviewed the Fund's investment performance by reviewing the Fund's
return on a net asset value and market price basis for the three month, six
month, one year and since inception (August 25, 2005) periods ended December 31,
2008 and compared it to the net asset value and market price returns of a peer
group of closed-end funds selected by the Adviser, which also invest primarily
in domestic equity securities and which employ an index options selling strategy
or short equity securities ("peer group funds"), the performance of an open-end
fund managed by the Sub-Adviser with the same investment strategy as the Fund
and the Fund's benchmark indices (the S&P 500 Index and the CBOE Buy-Write (BXM)
Index) for the same time periods. The Board also considered that the Adviser
does not directly control investment performance but had delegated such duties
to the Subadviser.

The Board considered the Fund's advisory fee (which includes the subadvisory fee
paid to the Subadviser) and expense ratio to the peer group of funds and to the
advisory fee that the Adviser charges to other closed-end funds for which it
serves as adviser. The Board also reviewed the mean and median advisory fees and
expense ratios of the peer group of funds.

With respect to the costs of services to be provided and profits realized by the
Adviser from its relationship to the Fund, the Board reviewed information
regarding the revenues the Adviser received under the Investment Advisory
Agreement as well as the estimated direct and indirect costs the Adviser incurs
in providing the services described in the Investment Advisory Agreement,
including paying the subadvisory fees to the Subadviser.

The Board considered the extent to which economies of scale could be realized
with respect to the management of the Fund as the Fund grows and whether fee
levels reflect a reasonable sharing of such economies of scale for the benefit
of Fund investors and also considered the current assets of the Fund. Given the
size of the Fund, the Board does not anticipate significant economies of scale
in the coming year.

The Board considered other benefits available to the Adviser because of its
relationship to the Fund and noted that the administrative services fees
received by the Adviser from serving as administrator to the Fund provided it
with additional revenue.


SUBADVISORY AGREEMENT
With respect to the nature, extent and quality of services provided by the
Subadviser, the Board considered the qualifications, experience, good reputation
and skills of the Subadviser's portfolio management and other key personnel. The
Board considered the Subadviser's ability to achieve the Fund's investment
objective of seeking a high level of current income and gains with a secondary
objective of long-term capital appreciation, and noted the Fund's performance
relative to its benchmark indices and the peer group of funds.

In evaluating investment performance, the Board reviewed the level of the Fund's
distributions and the Fund's investment performance on a net asset value basis
relative to the S&P 500 and BXM indices over relevant time periods. The Board
noted that for the year ended December 31, 2008 that the Fund had outperformed
the S&P 500 on a net asset value basis although the Fund's performance had been
negative on an absolute basis.



28 | Semiannual Report | June 30, 2009



OLA | Old Mutual/Claymore Long-Short Fund | BOARD CONSIDERATIONS REGARDING
INVESTMENT ADVISORY AGREEMENT AND SUBADVISORY AGREEMENT CONTRACT RE-APPROVAL
continued

The Board reviewed the subadvisory fee paid by the Adviser to the Subadviser and
compared it to the fees charged by the Subadviser to other accounts with
investment strategies comparable to the Fund's for which the Subadviser serves
as adviser or subadviser, including to a registered open-end investment company
with the same investment strategy as the Fund.

With respect to the costs of services to be provided and profits realized by the
Subadviser from its relationship to the Fund, the Board reviewed information
regarding the revenues the Subadviser received under the Subadvisory Agreement
and estimated direct and indirect allocated expenses of the Subadviser in
providing services under the Subadvisory Agreement.

The Board reviewed the extent to which economies of scale with respect to the
subadvisory services provided to the Fund would be realized as the Fund grows
and whether fee levels reflect a reasonable sharing of such economies of scale
for the benefit of Fund investors. Given the size of the Fund, the Board does
not anticipate significant economies of scale.

The Board considered other benefits derived by the Subadviser from its
relationship with the Fund. The Board noted the Subadviser's statement that it
does not enter into soft dollar arrangements and that it is not aware of any
other benefits from its relationship with the Fund.


OVERALL CONCLUSIONS
Based upon all of the information considered and the conclusions reached, the
Board determined that the terms of each Advisory Agreement continue to be fair
and reasonable, taking into consideration the costs of services to be provided
and profit realized, economies of scale and other benefits available to the
Adviser and Sub-Adviser.



                                          Semiannual Report | June 30, 2009 | 29



OLA | Old Mutual/Claymore Long-Short Fund

Fund INFORMATION |


BOARD OF TRUSTEES
Matthew J. Appelstein*
Randall C. Barnes
Steven D. Cosler
Nicholas Dalmaso**
Robert M. Hamje
L. Kent Moore
Ronald A. Nyberg
Ronald E. Toupin, Jr.

*    Trustee is an "interested person" of the Fund as defined in the Investment
     Company Act of 1940, as amended, as a result of his position as an officer
     of Old Mutual Asset Management, the parent company of the Fund's
     Sub-Adviser.

**   Trustee is an "interested person" of the Fund as defined in the Investment
     Company Act of 1940, as amended, as a result of his former position as an
     officer of, and his equity ownership in, the Fund's Investment Adviser and
     certain of its affiliates.


OFFICERS

J. Thomas Futrell
Chief Executive Officer

Kevin Robinson
Chief Legal Officer

Steven M. Hill
Chief Accounting Officer, Chief
Financial Officer and Treasurer

Mark Mathiasen
Secretary

Bruce Saxon
Chief Compliance Officer

INVESTMENT ADVISER
Claymore Advisors, LLC
Lisle, Illinois

INVESTMENT SUB-ADVISER
Analytic Investors, LLC
Los Angeles, California

ADMINISTRATOR
Claymore Advisors, LLC
Lisle, Illinois

ACCOUNTING AGENT, CUSTODIAN
AND TRANSFER AGENT
The Bank of New York Mellon
New York, New York

LEGAL COUNSEL
Skadden, Arps, Slate,
Meagher & Flom LLP
Chicago, Illinois

INDEPENDENT REGISTERED PUBLIC
ACCOUNTING FIRM
Ernst & Young LLP
Chicago, Illinois


PRIVACY PRINCIPLES OF OLD MUTUAL/CLAYMORE LONG-SHORT FUND FOR SHAREHOLDERS
The Fund is committed to maintaining the privacy of its shareholders and to
safeguarding its non-public personal information. The following information is
provided to help you understand what personal information the Fund collects, how
we protect that information and why, in certain cases, we may share information
with select other parties.

Generally, the Fund does not receive any non-public personal information
relating to its shareholders, although certain non-public personal information
of its shareholders may become available to the Fund. The Fund does not disclose
any non-public personal information about its shareholders or former
shareholders to anyone, except as permitted by law or as is necessary in order
to service shareholder accounts (for example, to a transfer agent or third party
administrator).

The Fund restricts access to non-public personal information about the
shareholders to Claymore Advisors, LLC employees with a legitimate business need
for the information. The Fund maintains physical, electronic and procedural
safeguards designed to protect the non-public personal information of its
shareholders.

QUESTIONS CONCERNING YOUR SHARES OF OLD MUTUAL/CLAYMORE LONG-SHORT FUND?

o    If your shares are held in a Brokerage Account, contact your Broker.

o    If you have physical possession of your shares in certificate form, contact
     the Fund's Custodian and Transfer Agent:
     The Bank of New York Mellon, 101 Barclay 11E, New York, New York 12086
     (866) 488-3559

This report is sent to shareholders of Old Mutual/Claymore Long-Short Fund for
their information. It is not a Prospectus, circular or representation intended
for use in the purchase or sale of shares of the Fund or of any securities
mentioned in this report.

A description of the Fund's proxy voting policies and procedures related to
portfolio securities is available without charge, upon request, by calling the
Fund at (866) 882-0688.

Information regarding how the Fund voted proxies for portfolio securities, if
applicable, during the most recent 12-month period ended June 30, is also
available, without charge and upon request by calling (866) 882-0688, by
visiting Claymore's website at www.claymore/ola or by accessing the Fund's Form
N-PX on the U.S. Securities and Exchange Commission's ("SEC") website at
www.sec.gov.

The Fund files its complete schedule of portfolio holdings with the SEC for the
first and third quarters of each fiscal year on Form N-Q. The Fund's Form N-Q is
available on the SEC website at www.sec.gov or by visiting Claymore's website at
www.claymore/ola. The Fund's Form N-Q may also be viewed and copied at the SEC's
Public Reference Room in Washington, DC; information on the operation of the
Public Reference Room may be obtained by calling (800) SEC-0330.

In August 2009, the Fund submitted a CEO annual certification to the NYSE in
which the Fund's principal executive officer certified that he was not aware, as
of the date of the certification, of any violation by the Fund of the NYSE's
Corporate Governance listing standards. In addition, as required by Section 302
of the Sarbanes-Oxley Act of 2002 and related SEC rules, the Fund's principal
executive and principal financial officers have made quarterly certifications,
included in filings with the SEC on Forms N-CSR and N-Q, relating to, among
other things, the Fund's disclosure controls and procedures and internal control
over financial reporting.

Notice is hereby given in accordance with Section 23(c) of the Investment
Company Act of 1940 that the Fund may from time to time purchase its shares of
common stock in the open market.



                                          Semiannual Report | June 30, 2009 | 31



OLA | Old Mutual/Claymore Long-Short Fund

About the FUND MANAGER |

ANALYTIC INVESTORS, LLC
Analytic Investors specializes in the application of systematic investment
processes to evaluate and exploit opportunities in the global equity, fixed
income and derivative securities markets. Based in Los Angeles and wholly owned
by Old Mutual plc, Analytic employs 35 professionals and manages more than $8
billion.
The firm manages a range of traditional, long-only equity products as well as a
number of absolute return strategies. The firm was founded in 1970 and, since
that time, has focused on delivering valued-added, risk-controlled investment
strategies to its range of institutional, fund-of-fund, and high net worth
clients.


INVESTMENT PHILOSOPHY
Analytic's philosophy is anchored in the conviction that the systematic
application of quantitative techniques to assess opportunity has the potential
to deliver quality, risk-adjusted performance, regardless of market cycle.
Analytic's quantitative methods bring together the best attributes of individual
security selection and unbiased portfolio modeling, yielding a management style
that is both disciplined and responsive.


INVESTMENT PROCESS
Analytic's innovative research seeks to uncover the factors that are driving
performance and are likely to be important going forward. Two core beliefs
underlie the firm's investment process:

     o    The attractiveness of every security is determined by a multitude of
          factors that can be measured.

     o    The desirability of a security's characteristics change with economic
          conditions.

Sophisticated quantitative techniques enable Analytic to simultaneously analyze
a variety of unique characteristics - such as relative valuation, growth
potential, historical returns, liquidity and risk - in an effort to identify and
exploit opportunities. Analytic uses thorough statistical analysis in an attempt
to identify the merits of each security as well as the relationships between
each security's measurable characteristics that may be driving its performance.

Analytic's proprietary multi-factor return models are applied in a
risk-controlled environment. The firm's highly evolved and successful approach,
supported by the research efforts of its investment team, capitalizes on
opportunity while neutralizing systematic market exposure and overall risk.







CLAYMORE SECURITIES, INC.
2455 Corporate West Drive
Lisle, IL 60532
Member FINRA/SIPC
(08/09)                                                                  OLA
                                                                        LISTED
            NOT FDIC-INSURED | NOT BANK-GUARANTEED | MAY LOSE VALUE     NYSE(R)


                                                                    OLA-SAR-0609



ITEM 2. CODE OF ETHICS.

Not applicable for a semi-annual reporting period.

ITEM 3. AUDIT COMMITTEE FINANCIAL EXPERT.

Not applicable for a semi-annual reporting period.

ITEM 4. PRINCIPAL ACCOUNTANT FEES AND SERVICES.

Not applicable for a semi-annual reporting period.

ITEM 5. AUDIT COMMITTEE OF LISTED REGISTRANTS.

Not applicable for a semi-annual reporting period.

ITEM 6. SCHEDULE OF INVESTMENTS.

The Schedule of Investments is included as part of Item 1.

ITEM 7. DISCLOSURE OF PROXY VOTING POLICIES AND PROCEDURES FOR CLOSED-END
MANAGEMENT INVESTMENT COMPANIES.

Not applicable for a semi-annual reporting period.

ITEM 8. PORTFOLIO MANAGERS OF CLOSED-END MANAGEMENT INVESTMENT COMPANIES.

     (a)  Not applicable for a semi-annual reporting period.

     (b)  There has been no change, as of the date of this filing, in the
          Portfolio Manager identified in response to paragraph (a) (1) of this
          item in the registrant's most recent annual report on Form N-CSR.

ITEM 9. PURCHASES OF EQUITY SECURITIES BY CLOSED-END MANAGEMENT INVESTMENT
COMPANY AND AFFILIATED PURCHASERS.

None.

ITEM 10. SUBMISSION OF MATTERS TO A VOTE OF SECURITY HOLDERS.

The registrant has not made any material changes to the procedures by which
shareholders may recommend nominees to the registrant's Board of Trustees.

ITEM 11. CONTROLS AND PROCEDURES.

(a) The registrant's principal executive officer and principal financial officer
have evaluated the registrant's disclosure controls and procedures (as defined
in Rule 30a3(c) under the Investment Company Act of 1940) as of a date within 90
days of this filing and have concluded based on such evaluation, that the
registrant's disclosure controls and procedures were effective, as of that date,
in



ensuring that information required to be disclosed by the registrant in this
Form N-CSR was recorded, processed, summarized, and reported within the time
periods specified in the Securities and Exchange Commission's rules and forms.

(b) There were no changes in the registrant's internal control over financial
reporting (as defined in Rule 30a-3(d) under the Investment Company Act of 1940)
that occurred during the registrant's second fiscal quarter of the period
covered by this report that have materially affected, or are reasonably likely
to materially affect, the registrant's internal control over financial
reporting.

ITEM 12. EXHIBITS.

(a)(1) Not applicable.

(a)(2) Certifications of principal executive officer and principal financial
officer pursuant to Rule 30a-2(a) of the Investment Company Act of 1940.

(a)(3) Not Applicable.

(b) Certifications of principal executive officer and principal financial
officer pursuant to Rule 30a-2(b) of the Investment Company Act of 1940.



                                   SIGNATURES



     Pursuant to the requirements of the Securities Exchange Act of 1934 and the
Investment Company Act of 1940, the registrant has duly caused this report to be
signed on its behalf by the undersigned, thereunto duly authorized.

(Registrant) Old Mutual/Claymore Long-Short Fund
            ------------------------------------

By:      /s/ J. Thomas Futrell
         -----------------------------------------------------------------------

Name:    J. Thomas Futrell

Title:   Chief Executive Officer

Date:    September 2, 2009

     Pursuant to the requirements of the Securities Exchange Act of 1934 and the
Investment Company Act of 1940, this report has been signed by the following
persons on behalf of the registrant and in the capacities and on the dates
indicated.

By:      /s/ J. Thomas Futrell
         -----------------------------------------------------------------------

Name:    J. Thomas Futrell

Title:   Chief Executive Officer

Date:    September 2, 2009

By:      /s/ Steven M. Hill
         -----------------------------------------------------------------------

Name:    Steven M. Hill

Title:   Treasurer and Chief Financial Officer

Date:    September 2, 2009