FLAHERTY & CRUMRINE PREFERRED INCOME OPPORTUNITY FUND To the Shareholders of Flaherty & Crumrine Preferred Income Opportunity Fund: The Fund delivered a second consecutive quarter of double-digit returns as financial markets continued to recover from lows hit earlier this year. During the three-month period ended August 31st, total return on net asset value was +25.2%, and total return on market value of Fund shares was +12.9%. As the worst of the financial crisis appears to be behind us, prices on most securities in the Fund's portfolio rose during the quarter. Although the credit outlook for some issuers remains speculative and the prices of their securities remain depressed, many securities that suffered the biggest declines earlier in the year staged the most dramatic recoveries. That being said, while prices in general are much higher than just three months ago, they remain well below the highs reached in recent years. There should be further recovery if the markets continue to normalize as we expect. The strong performance over the past two quarters occurred despite the negative impact of our investments in a few troubled companies. During the past quarter, Colonial Bank was shut down by regulators. At this point, we are assuming there will be no additional income earned and minimal principal recovery on our investment in its parent, Colonial BancGroup, Inc. Two additional credits, FBOP Bancorp and CIT Group, suspended distributions on the securities owned by the Fund. Both companies are currently exploring strategies to improve their financial condition. One year ago, the world's financial system was on the brink of collapse. In the blink of an eye, we went from a world in which anyone with a pulse could get a loan to a virtual shutdown of the capital markets. Investors, large and small, appeared ready to stuff money in a mattress rather than hand it over to a bank or money market fund. Access to short-term liquidity, the life blood of business, largely disappeared, and long-term financing was virtually unobtainable. Banks simply stopped lending (not only to long-time customers, but even more troublesome, to other banks), and capital market investors were in no mood to provide new financing. When compared to broader credit markets, the preferred market has a much greater concentration in financial companies. In addition, the majority of preferred issues are long-term and consequently tend to have more volatile prices than other fixed-income instruments. As a result, the performance of the preferred market (and the Fund) was dismal throughout the early part of the financial crisis. After one year, and massive amounts of government intervention, we see signs of recovery and perhaps a greater sense of rationality in the markets. On more than one occasion we've expressed our opinion that market volatility was exacerbated by excessive amounts of leverage. We underestimated the extent to which price declines could trigger selling by over-leveraged investors, producing an accelerating downward price spiral. We learned some valuable lessons during this financial chaos. We improved our analytic tools (and hopefully developed a more refined sense of smell) to help us discern changes in fundamental value from a leverage-fed frenzy. We further refined our credit criteria to help us identify riskier issuers earlier in the credit cycle. And, as leveraged investors ourselves, we have a keener appreciation for liquidity in the Fund's portfolio. We believe these lessons will improve ongoing management of the Fund. Don't expect wholesale changes, but we would not be doing our job if we did not adapt to this new, more turbulent environment. For instance, the Fund suspended its hedging strategy last year, not because we no longer believe in hedging but because we did not think it would work in a crisis environment. At some point in the future, we anticipate reinstating the Fund's hedging strategy. Similarly, we have increased the portfolio's emphasis on liquid issues and issuers. By doing so, the Fund may give up some current income, but we believe this provides greater flexibility in managing the portfolio and its leverage for the benefit of shareholders. In our last letter we indicated that the Fund was in the process of replacing all remaining shares of Auction Preferred Stock with bank debt. The switch is complete and the Fund's leverage is now comprised entirely of debt. While the breakdown in the auction preferred stock market made the change necessary, the Fund already is realizing some benefits from the new leverage. Foremost among these benefits are lower borrowing expense and greater flexibility in managing the portfolio. All markets have endured tremendous upheaval over the past year. More change is on the horizon, as the financial system moves from crisis to recovery. The Fund will continue to assess and adapt to this new market environment. We take that responsibility seriously, and we appreciate the support that shareholders have given us. More information is always available on the Fund's website, including discussion of many of the topics in this letter. In addition, our thoughts on the economic outlook are published quarterly and posted to the site. We encourage you to visit the website at www.preferredincome.com. Sincerely, /s/ Donald F. Crumrine /s/ Robert M. Ettinger Donald F. Crumrine Robert M. Ettinger Chairman of the Board President October 15, 2009 2 Flaherty & Crumrine Preferred Income Opportunity Fund Incorporated PORTFOLIO OVERVIEW AUGUST 31, 2009 (UNAUDITED) FUND STATISTICS ON 8/31/09 Net Asset Value $ 7.00 Market Price $ 6.66 Discount 4.86% Yield on Market Price 9.01% Common Stock Shares Outstanding 11,906,765 MOODY'S RATINGS % OF NET ASSETS+ --------------- ---------------- AA 0.3% A 17.8% BBB 56.2% BB 20.2% Below "BB" 1.0% Not Rated 2.9% ---- Below Investment Grade* 16.2% * BELOW INVESTMENT GRADE BY BOTH MOODY'S AND S&P. (PIE CHART) INDUSTRY CATEGORIES % OF NET ASSETS+ ------------------- ---------------- Financial Services 1% Other 2% Banking 39% Utilities 26% Insurance 24% Energy 8% TOP 10 HOLDINGS BY ISSUER % OF NET ASSETS+ ------------------------- ---------------- Banco Santander 5.3% Liberty Mutual Group 5.1% Metlife 4.6% Sovereign Bancorp 4.6% Southern California Edison 3.9% Goldman Sachs 3.6% Comerica 3.5% Capital One Financial 3.5% Dominion Resources 3.1% Interstate Power & Light 3.0% % OF NET ASSETS**+ ------------------ Holdings Generating Qualified Dividend Income (QDI) for Individuals 45% Holdings Generating Income Eligible for the Corporate Dividends Received Deduction (DRD) 34% ** THIS DOES NOT REFLECT YEAR-END RESULTS OR ACTUAL TAX CATEGORIZATION OF FUND DISTRIBUTIONS. THESE PERCENTAGES CAN, AND DO, CHANGE, PERHAPS SIGNIFICANTLY, DEPENDING ON MARKET CONDITIONS. INVESTORS SHOULD CONSULT THEIR TAX ADVISOR REGARDING THEIR PERSONAL SITUATION. + NET ASSETS INCLUDES ASSETS ATTRIBUTABLE TO THE USE OF LEVERAGE. 3 Flaherty & Crumrine Preferred Income Opportunity Fund Incorporated PORTFOLIO OF INVESTMENTS AUGUST 31, 2009 (UNAUDITED) SHARES/$ PAR VALUE ------------ ------------ PREFERRED SECURITIES -- 96.4% BANKING -- 38.6% $ 3,000,000 Astoria Capital Trust I, 9.75% 11/01/29, Series B .............................. $ 3,012,129 Banco Santander: 21,100 Adj. Rate Pfd. .............................................................. 333,011**(1)(2) 235,750 6.50% Pfd. .................................................................. 5,458,202**(1)(2) 22,750 6.80% Pfd. .................................................................. 548,332**(1)(2) $ 2,250,000 Barclays Bank PLC, 6.278% ...................................................... 1,600,312**(1)(2) 45,000 BB&T Capital Trust VI, 9.60% Pfd. .............................................. 1,178,100(1) $ 5,300,000 Capital One Capital III, 7.686% 08/15/36 ....................................... 4,187,000(1) CIT Group, Inc.: 22,500 5.189% Pfd., Series B ....................................................... 97,735*+ 211,200 6.35% Pfd., Series A ........................................................ 583,440*+ 45,000 Cobank, ACB, 7.00% Pfd., 144A**** .............................................. 1,570,783*(1) $ 4,500,000 Colonial BancGroup, 7.114%, 144A**** ........................................... 78,750+ $ 6,170,000 Comerica Capital Trust II, 6.576% 02/20/37 ..................................... 4,257,300(1) 4,500 FBOP Corporation, Adj. Rate Pfd., 144A**** ..................................... 192,656*+ 890 First Republic Preferred Capital Corporation, 10.50% Pfd., 144A**** ............ 805,450 22,500 First Republic Preferred Capital Corporation II, 8.75% Pfd., Series B, 144A**** .......................................................... 492,892 2,500 First Tennessee Bank, Adj. Rate Pfd., 144A**** ................................. 1,013,281*(1) $ 500,000 First Tennessee Capital II, 6.30% 04/15/34, Series B ........................... 282,724 Goldman Sachs: $ 4,600,000 Capital II, 5.793% .......................................................... 3,381,000(1) 11 Pass-Through Certificates, Class B, 144A**** ................................ 182,600*+ 3,500 STRIPES Custodial Receipts, Pvt. ............................................ 721,000* HSBC USA, Inc.: 176,000 Adj. Rate Pfd., Series G .................................................... 3,284,600*(1) 2,500 $2.8575 Pfd. ................................................................ 96,750*(1) 15,300 Keycorp Capital VIII, 7.00% Pfd. 06/15/66 ...................................... 293,951 10,000 Keycorp Capital X, 8.00% Pfd. .................................................. 213,650 $ 450,000 Lloyds Banking Group PLC, 6.657%, 144A**** ..................................... 193,822**(2) 28,000 PFGI Capital Corporation, 7.75% Pfd. ........................................... 656,250(1) 99,000 PNC Financial Services, 9.875% Pfd., Series F .................................. 2,635,628*(1) $ 300,000 PNC Preferred Funding Trust III, 8.70%, 144A**** ............................... 264,694(1) 122,700 Sovereign Bancorp, 7.30% Pfd., Series C ........................................ 2,934,064*(1) 9,875 Sovereign Capital Trust V, 7.75% Pfd. 05/22/36 ................................. 226,458(1) 4 Flaherty & Crumrine Preferred Income Opportunity Fund Incorporated PORTFOLIO OF INVESTMENTS (CONTINUED) AUGUST 31, 2009 (UNAUDITED) SHARES/$ PAR VALUE ------------ ------------ PREFERRED SECURITIES -- (CONTINUED) BANKING -- (CONTINUED) 2,600 Sovereign REIT, 12.00% Pfd., Series A, 144A**** ........................... $ 2,346,500 U.S. Bancorp, Auction Pass-Through Trust, Cl. B: 9 Series 2006-5, Variable Rate Pfd., 144A**** ............................ 225*+ 9 Series 2006-6, Variable Rate Pfd., 144A**** ............................ 225*+ $ 900,000 Washington Mutual, 9.75%, 144A**** ........................................ 13,500++ $ 1,400,000 Webster Capital Trust IV, 7.65% 06/15/37 .................................. 826,000(1) Wells Fargo & Company: $ 2,000,000 7.98%, Series K ........................................................ 1,810,000*(1) 22,500 8.00% Pfd., Series J ................................................... 552,375*(1) ------------ 46,325,389 ------------ FINANCIAL SERVICES -- 0.5% $ 250,000 Ameriprise Financial, Inc., 7.518% 06/01/66 ............................... 196,250(1) $ 500,000 General Electric Capital Corporation, 6.375% 11/15/67 ..................... 404,356 Lehman Brothers Holdings, Inc.: 45,800 5.67% Pfd., Series D ................................................... 16,946*++ 9,500 5.94% Pfd., Series C ................................................... 3,135*++ 25,000 6.50% Pfd., Series F ................................................... 2,813*++ 13,400 7.95% Pfd. ............................................................. 1,273*++ ------------ 624,773 ------------ INSURANCE -- 21.8% $ 1,000,000 Ace Capital Trust II, 9.70% 04/01/30 ...................................... 1,003,484(1)(2) Arch Capital Group Ltd.: 12,400 7.875% Pfd., Series B .................................................. 284,239**(1)(2) 22,000 8.00% Pfd., Series A ................................................... 535,315**(1)(2) AXA SA: $ 1,200,000 6.379%, 144A**** ....................................................... 894,000**(1)(2) $ 3,000,000 6.463%, 144A**** ....................................................... 2,235,000**(1)(2) 29,700 Axis Capital Holdings, 7.50% Pfd., Series B ............................... 1,936,069(1)(2) 90,000 Delphi Financial Group, 7.376% Pfd. 05/15/37 .............................. 1,552,500(1) $ 3,250,000 Everest Re Holdings, 6.60% 05/15/37 ....................................... 2,291,250(1) Liberty Mutual Group: $ 2,000,000 7.80% 03/15/37, 144A**** ............................................... 1,430,000(1) $ 4,400,000 10.75% 06/15/58, 144A**** .............................................. 3,938,000(1) $ 467,000 MetLife Capital Trust IV, 7.875% 12/15/37, 144A**** ....................... 417,965(1) $ 4,133,000 MetLife Capital Trust X, 9.25% 04/08/38, 144A**** ......................... 4,029,212(1) $ 1,000,000 MetLife, Inc., 10.75% 08/01/39 ............................................ 1,127,917(1) 5 Flaherty & Crumrine Preferred Income Opportunity Fund Incorporated PORTFOLIO OF INVESTMENTS (CONTINUED) AUGUST 31, 2009 (UNAUDITED) SHARES/$ PAR VALUE ------------ ------------ PREFERRED SECURITIES -- (CONTINUED) INSURANCE -- (CONTINUED) Principal Financial Group: 5,000 5.563% Pfd., Series A ....................................................... $ 317,500* 72,700 6.518% Pfd., Series B ....................................................... 1,319,687*(1) Renaissancere Holdings Ltd.: 56,050 6.08% Pfd., Series C ........................................................ 1,041,409**(1)(2) 12,900 6.60% Pfd., Series D ........................................................ 264,192**(1)(2) 10,700 7.30% Pfd., Series B ........................................................ 234,785**(2) 115,500 Scottish Re Group Ltd., 7.25% Pfd. ............................................. 284,419**(2)+ $ 1,060,000 USF&G Capital, 8.312% 07/01/46, 144A**** ....................................... 1,019,184(1) ------------ 26,156,127 ------------ UTILITIES -- 25.6% 6,579 Baltimore Gas & Electric Company, 6.70% Pfd., Series 1993 ...................... 585,531*(1) 2,780 Central Vermont Public Service Corporation, 8.30% Sinking Fund Pfd., Pvt. ...... 281,141* Dominion Resources, Inc.: $ 2,700,000 7.50% ....................................................................... 2,216,781(1) 56,500 8.375% Pfd., Series A ....................................................... 1,497,250(1) Georgia Power Company: 3,555 6.125% Pfd. ................................................................. 86,253*(1) 5,000 6.50% Pfd., Series 2007A .................................................... 480,469*(1) Gulf Power Company: 16,500 6.00% Pfd., Series 1 ........................................................ 1,335,578*(1) 13,000 6.45% Pfd., Series 2007A .................................................... 1,219,121*(1) 30,500 Indianapolis Power & Light Company, 5.65% Pfd. ................................. 2,446,673*(1) 129,900 Interstate Power & Light Company, 8.375% Pfd., Series B ........................ 3,645,319*(1) Pacific Enterprises: 15,935 $4.50 Pfd. .................................................................. 1,220,023*(1) 8,935 $4.75 Pfd., Series 53 ....................................................... 710,054*(1) $ 1,500,000 PECO Energy Capital Trust III, 7.38% 04/06/28, Series D ........................ 1,275,346(1) $ 4,500,000 Puget Sound Energy, Inc., 6.974% 06/01/67 ...................................... 3,613,023(1) 60,000 Southern California Edison, 6.00% Pfd., Series C ............................... 4,726,878*(1) $ 2,780,000 Southern Union Company, 7.20% 11/01/66 ......................................... 2,091,950 $ 750,000 TXU Electric Capital V, 8.175% 01/30/37 ........................................ 341,250 Union Electric Company: 5,700 4.56% Pfd. .................................................................. 380,475* 10,156 $7.64 Pfd. .................................................................. 987,989*(1) $ 2,000,000 Wisconsin Energy Corporation, 6.25% 05/15/67 ................................... 1,582,262(1) ------------ 30,723,366 ------------ 6 Flaherty & Crumrine Preferred Income Opportunity Fund Incorporated PORTFOLIO OF INVESTMENTS (CONTINUED) AUGUST 31, 2009 (UNAUDITED) SHARES/$ PAR VALUE ------------ ------------ PREFERRED SECURITIES -- (CONTINUED) ENERGY -- 7.9% $ 4,000,000 Enbridge Energy Partners LP, 8.05% 10/01/37 ................................. $ 3,379,916(1) Enterprise Products Partners: $ 1,000,000 7.034% 01/15/68 .......................................................... 821,217 $ 2,460,000 8.375% 08/01/66, Series A ................................................ 2,136,709 3,000 Kinder Morgan GP, Inc., 8.33% Pfd., 144A**** ................................ 2,738,625* $ 500,000 Teppco Partners LP, 7.00% 06/01/67 .......................................... 397,212 ------------ 9,473,679 ------------ MISCELLANEOUS INDUSTRIES -- 2.0% 35,000 Ocean Spray Cranberries, Inc., 6.25% Pfd., 144A**** ......................... 2,338,438*(1) ------------ 2,338,438 ------------ TOTAL PREFERRED SECURITIES (Cost $ 138,451,863) ..................................................... 115,641,772 ------------ CORPORATE DEBT SECURITIES -- 2.0% FINANCIAL SERVICES -- 0.2% 10,000 Ameriprise Financial, Inc., 7.75% 06/15/39 .................................. 240,025(1) ------------ 240,025 ------------ INSURANCE -- 1.8% $ 1,050,000 Liberty Mutual Insurance, 7.697% 10/15/97, 144A**** ......................... 699,238(1) $ 2,000,000 UnumProvident Corporation, 7.25% 03/15/28, Senior Notes ..................... 1,485,472(1) ------------ 2,184,710 ------------ TOTAL CORPORATE DEBT SECURITIES (Cost $ 2,467,177) ....................................................... 2,424,735 ------------ MONEY MARKET FUND -- 0.6% 738,696 BlackRock Provident Institutional, T-Fund ................................... 738,696 ------------ TOTAL MONEY MARKET FUND (Cost $738,696) .......................................................... 738,696 ------------ 7 Flaherty & Crumrine Preferred Income Opportunity Fund Incorporated PORTFOLIO OF INVESTMENTS (CONTINUED) AUGUST 31, 2009 (UNAUDITED) VALUE ------------ TOTAL INVESTMENTS (Cost $141,657,736***) .............................................. 99.0% $118,805,203 OTHER ASSETS AND LIABILITIES (Net) .................................................... 1.0% 1,188,361 ----- ------------ NET ASSETS BEFORE LOAN ................................................................ 100.0%+++ $119,993,564 ----- ------------ LOAN PRINCIPAL BALANCE ................................................................ (36,600,000) ------------ TOTAL NET ASSETS AVAILABLE TO COMMON STOCK ............................................ $ 83,393,564 ============ ---------- * Securities eligible for the Dividends Received Deduction and distributing Qualified Dividend Income. ** Securities distributing Qualified Dividend Income only. *** Aggregate cost of securities held. **** Securities exempt from registration under Rule 144A of the Securities Act of 1933. These securities may be resold in transactions exempt from registration to qualified institutional buyers. At August 31, 2009, these securities amounted to $26,895,040 or 22.4% of net assets. These securities have been determined to be liquid under the guidelines established by the Board of Directors. (1) All or a portion of this security is pledged as collateral for the Fund's loan. The total value of such securities was $95,889,241 at August 31, 2009. (2) Foreign Issuer. + Non-income producing. ++ The issuer has filed for bankruptcy protection. As a result, the Fund may not be able to recover the principal invested and also does not expect to receive income on this security going forward. +++ The percentage shown for each investment category is the total value of that category as a percentage of net assets before the loan. ABBREVIATIONS: PFD. -- Preferred Securities PVT. -- Private Placement Securities REIT -- Real Estate Investment Trust STRIPES -- Structured Residual Interest Preferred Enhanced Securities 8 Flaherty & Crumrine Preferred Income Opportunity Fund Incorporated STATEMENTS OF CHANGES IN NET ASSETS AVAILABLE TO COMMON STOCK(1) FOR THE PERIOD FROM DECEMBER 1, 2008 THROUGH AUGUST 31, 2009 (UNAUDITED) VALUE ------------ OPERATIONS: Net investment income .......................................................... $ 6,309,282 Net realized gain/(loss) on investments sold during the period ................. (11,887,895) Change in net unrealized appreciation/depreciaton of investments ............... 39,124,086 Distributions to APS* Shareholders from net investment income, including changes in accumulated undeclared distributions ..................................... (936,183) ------------ NET INCREASE IN NET ASSETS RESULTING FROM OPERATIONS ........................... 32,609,290 DISTRIBUTIONS: Dividends paid from net investment income to Common Stock Shareholders(2) ...... (5,339,094) ------------ TOTAL DISTRIBUTIONS TO COMMON STOCK SHAREHOLDERS ............................... (5,339,094) FUND SHARE TRANSACTIONS: Increase from shares issued under the Dividend Reinvestment and Cash Purchase Plan ............................................................... 375,985 ------------ NET INCREASE IN NET ASSETS AVAILABLE TO COMMON STOCK RESULTING FROM FUND SHARE TRANSACTIONS .......................................................... 375,985 ------------ NET INCREASE IN NET ASSETS AVAILABLE TO COMMON STOCK FOR THE PERIOD ............... $ 27,646,181 ============ NET ASSETS AVAILABLE TO COMMON STOCK: Beginning of period ............................................................ $ 55,747,383 Net increase in net assets during the period ................................... 27,646,181 ------------ End of period .................................................................. $ 83,393,564 ============ ---------- * Auction Preferred Stock. (1) These tables summarize the nine months ended August 31, 2009 and should be read in conjunction with the Fund's audited financial statements, including footnotes, in its Annual Report dated November 30, 2008. (2) May include income earned, but not paid out, in prior fiscal year. 9 Flaherty & Crumrine Preferred Income Opportunity Fund Incorporated FINANCIAL HIGHLIGHTS(1) FOR THE PERIOD FROM DECEMBER 1, 2008 THROUGH AUGUST 31, 2009 (UNAUDITED) FOR A COMMON STOCK SHARE OUTSTANDING THROUGHOUT THE PERIOD. PER SHARE OPERATING PERFORMANCE: Net asset value, beginning of period .................................. $ 4.71 ----------- INVESTMENT OPERATIONS: Net investment income ................................................. 0.53 Net realized and unrealized gain/(loss) on investments ................ 2.29 DISTRIBUTIONS TO APS* SHAREHOLDERS: From net investment income ............................................ (0.08) ----------- Total from investment operations ...................................... 2.74 ----------- DISTRIBUTIONS TO COMMON STOCK SHAREHOLDERS: From net investment income ............................................ (0.45) ----------- Total distributions to Common Stock Shareholders ...................... (0.45) ----------- Net asset value, end of period ........................................ $ 7.00 =========== Market value, end of period ........................................... $ 6.66 =========== Common Stock shares outstanding, end of period ........................ 11,906,765 =========== RATIOS TO AVERAGE NET ASSETS AVAILABLE TO COMMON STOCK SHAREHOLDERS: Net investment income+ ................................................ 13.44%** Net investment income, including payments to APS Shareholders+ ........ 11.44%** Operating expenses including interest expense ......................... 2.64%** Operating expenses excluding interest expense ......................... 2.47%** SUPPLEMENTAL DATA:++ Portfolio turnover rate ............................................... 47%*** Net assets before loan, end of period (in 000's) ...................... $ 119,994 Ratio of operating expenses including interest expense(2) to net assets before loan and APS ................................................ 1.60%** Ratio of operating expenses excluding interest expense(2) to net assets before loan and APS ................................................ 1.49%** (1) These tables summarize the nine months ended August 31, 2009 and should be read in conjunction with the Fund's audited financial statements, including footnotes, in its Annual Report dated November 30, 2008. (2) Does not include distributions to APS Shareholders. * Auction Preferred Stock. ** Annualized. *** Not Annualized. + The net investment income ratios reflect income net of operating expenses, including interest expense. ++ Information presented under heading Supplemental Data includes APS and loan principal balance. 10 Flaherty & Crumrine Preferred Income Opportunity Fund Incorporated FINANCIAL HIGHLIGHTS (CONTINUED) PER SHARE OF COMMON STOCK (UNAUDITED) TOTAL DIVIDEND DIVIDENDS NET ASSET NYSE REINVESTMENT PAID VALUE CLOSING PRICE PRICE(1) --------- --------- ------------- ------------ December 31, 2008 .. $0.0500 $5.14 $4.60 $4.89 January 30, 2009 ... 0.0500 4.96 4.75 4.84 February 27, 2009 .. 0.0500 4.23 4.50 4.28 March 31, 2009 ..... 0.0500 4.30 4.43 4.30 April 30, 2009 ..... 0.0500 4.66 5.03 4.78 May 29, 2009 ....... 0.0500 5.72 6.04 5.74 June 30, 2009 ...... 0.0500 6.12 6.31 6.12 July 31, 2009 ...... 0.0500 6.55 6.47 6.55 August 31, 2009 .... 0.0500 7.00 6.66 6.74 ---------- (1) Whenever the net asset value per share of the Fund's Common Stock is less than or equal to the market price per share on the reinvestment date, new shares issued will be valued at the higher of net asset value or 95% of the then current market price. Otherwise, the reinvestment shares of Common Stock will be purchased in the open market. 11 Flaherty & Crumrine Preferred Income Opportunity Fund Incorporated NOTES TO FINANCIAL STATEMENTS (UNAUDITED) 1. AGGREGATE INFORMATION FOR FEDERAL INCOME TAX PURPOSES At August 31, 2009 the aggregate cost of securities for federal income tax purposes was $141,843,044, the aggregate gross unrealized appreciation for all securities in which there is an excess of value over tax cost was $8,242,130 and the aggregate gross unrealized depreciation for all securities in which there is an excess of tax cost over value was $31,279,971. 2. ADDITIONAL ACCOUNTING STANDARDS STATEMENT OF FINANCIAL ACCOUNTING STANDARDS NO. 157 "FAIR VALUE MEASUREMENTS" ("SFAS 157") In September 2006, the Financial Accounting Standards Board ("FASB") issued Statement of Financial Accounting Standards No. 157 "Fair Value Measurements" ("SFAS 157") effective for fiscal years beginning after November 15, 2007. 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. The Fund has adopted SFAS 157 as of December 1, 2007. The three levels of the fair value hierarchy under SFAS 157 are described below: - Level 1 - quoted prices in active markets for identical securities - Level 2 - other significant observable inputs (including quoted prices for similar securities, interest rates, prepayment speeds, credit risk, etc.) - Level 3 - significant unobservable inputs (including the Fund's own assumptions in determining the fair value of investments) In April 2009, FASB issued FASB Staff Position No. 157-4, "Determining Fair Value when the 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 is effective for fiscal years and interim periods ending after June 15, 2009. FSP 157-4 provides additional guidance for estimating fair value in accordance with SFAS 157, when the volume and level of activity for the asset or liability have significantly decreased. FSP 157-4 also includes guidance on identifying circumstances that indicate a transaction is not orderly. FSP 157-4 requires entities to describe the inputs and valuation techniques used to measure fair value and changes in those techniques and related inputs during the period. FSP 157-4 expands the three-level hierarchy disclosure and the level three-roll forward disclosure for each major security type as described in paragraph 19 of SFAS 115, "Accounting for Certain Investments in Debt and Equity Securities." 12 Flaherty & Crumrine Preferred Income Opportunity Fund Incorporated NOTES TO FINANCIAL STATEMENTS (UNAUDITED) (CONTINUED) The inputs or methodology used for valuing securities are not necessarily an indication of the risk associated with investing in those securities. A summary of the inputs used to value the Fund's net assets as of August 31, 2009 is as follows: LEVEL 2 LEVEL 3 TOTAL LEVEL 1 SIGNIFICANT SIGNIFICANT VALUE AT QUOTED OBSERVABLE UNOBSERVABLE AUGUST 31, 2009 PRICE INPUTS INPUTS --------------- ----------- ----------- ------------ Preferred Securities Banking $ 46,325,389 $21,052,611 $25,080,122 $192,656 Financial Services 624,773 24,167 600,606 -- Insurance 26,156,127 5,516,546 20,639,581 -- Utilities 30,723,366 5,228,822 25,494,544 -- Energy 9,473,679 -- 9,473,679 -- Miscellaneous Industries 2,338,438 -- 2,338,438 -- Corporate Debt Securities 2,424,735 240,025 2,184,710 -- Money Market Fund 738,696 738,696 -- -- ------------ ----------- ----------- -------- Total Investments $118,805,203 $32,800,867 $85,811,680 $192,656 ============ =========== =========== ======== The following is a reconciliation of Level 3 investments for which significant unobservable inputs were used to determine fair value: PREFERRED SECURITIES ------------------------------- TOTAL INVESTMENTS BANKING ----------------- ----------- BALANCE AS OF 11/30/08 ............................. $ -- $ -- Accrued discounts/premiums ......................... -- -- Realized gain/(loss) ............................... -- -- Change in unrealized appreciation/(depreciation) ... (2,169,844) (2,169,844) Net purchases/(sales) .............................. -- -- Transfer in and/or out of Level 3 .................. 2,362,500 2,362,500 ----------- ----------- BALANCE AS OF 8/31/09 .............................. $ 192,656 $ 192,656 13 Flaherty & Crumrine Preferred Income Opportunity Fund Incorporated NOTES TO FINANCIAL STATEMENTS (UNAUDITED) (CONTINUED) 3. SECTION 19 NOTICES Section 19 of the Investment Company Act of 1940 requires registered investment companies to include a notice with the payment of a dividend if a portion of that dividend may come from sources other than undistributed net income (other sources could include realized gains from the sale of securities and non-taxable return of capital). Copies of the Section 19 notices for the Fund are available on the website at www.preferredincome.com. The amounts and sources of distributions reported below are only estimates and are not being provided for tax reporting purposes. Form 1099-DIV will be sent to shareholders in January 2010 reporting the amount and tax characterization of distributions for the 2009 calendar year. SOURCE OF DISTRIBUTIONS AS OF 8/31/09 ------------------------------------- NET NET RETURN INVESTMENT REALIZED OF INCOME CAPITAL GAINS CAPITAL ---------- ------------- ------- Calendar 2009 Percentage of Total Distributions .. 95.0% 0.0% 5.0% 14 [This page intentionally left blank] (FLAHERTY & CRUMRINE LOGO) PREFERRED INCOME OPPORTUNITY FUND Quarterly Report August 31, 2009 www.preferredincome.com DIRECTORS Donald F. Crumrine, CFA Chairman of the Board David Gale Morgan Gust Karen H. Hogan Robert F. Wulf, CFA OFFICERS Donald F. Crumrine, CFA Chief Executive Officer Robert M. Ettinger, CFA President R. Eric Chadwick, CFA Chief Financial Officer, Vice President and Treasurer Chad C. Conwell Chief Compliance Officer, Vice President and Secretary Bradford S. Stone Vice President and Assistant Treasurer Laurie C. Lodolo Assistant Compliance Officer, Assistant Treasurer and Assistant Secretary INVESTMENT ADVISER Flaherty & Crumrine Incorporated e-mail: flaherty@pfdincome.com QUESTIONS CONCERNING YOUR SHARES OF FLAHERTY & CRUMRINE PREFERRED INCOME OPPORTUNITY FUND? - If your shares are held in a Brokerage Account, contact your Broker. - If you have physical possession of your shares in certificate form, contact the Fund's Transfer Agent & Shareholder Servicing Agent -- PNC Global Investment Servicing (U.S.) Inc. P.O. Box 43027 Providence, RI 02940-3027 1-800-331-1710 THIS REPORT IS SENT TO SHAREHOLDERS OF FLAHERTY & CRUMRINE PREFERRED INCOME OPPORTUNITY FUND INCORPORATED 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.