Winners of The Pimlico Special Since 1937
| Year |
Winner |
Age |
Jockey |
Trainer |
Owner |
Distance |
Time |
Purse |
Grade |
| 2013 | - | 1³/ | 0:00.00 | $300,000 | III | ||||
| 2012 | Alternation | 4 | Luis Quinonez | Donnie Von Hemel | Pin Oak Stable | 1³/ | 1:57.60 | $300,000 | III |
| 2011 | No Race | - | No Race | No Race | No Race | 1³/ | no race | no race | |
| 2010 | No Race | - | No Race | No Race | No Race | 1³/ | no race | no race | I |
| 2009 | No Race | - | No Race | No Race | No Race | 1³/ | no race | no race | I |
| 2008 | Student Council | 6 | Shaun Bridgmohan | Steve Asmussen | Millennium Farms | 1³/ | 1:54.87 | $250,000 | I |
| 2007 | No Race | - | No Race | No Race | No Race | 1³/ | no race | no race | I |
| 2006 | Invasor | 4 | Ramon Dominguez | Kiaran McLaughlin | Shadwell Stable | 1³/ | 1:54.40 | $500,000 | I |
| 2005 | Eddington | 4 | Eibar Coa | Mark A. Hennig | Willmott Stables | 1³/ | 1:58.05 | $500,000 | I |
| 2004 | Southern Image | 4 | Victor Espinoza | Michael Machowsky | Blahut Stables | 1³/ | 1:55.89 | $600,000 | I |
| 2003 | Mineshaft | 4 | Robby Albarado | Neil J. Howard | Farish/Webber/Elkins | 1³/ | 1:56.16 | $600,000 | I |
| 2002 | No Race | - | No Race | No Race | No Race | 1³/ | no race | no race | I |
| 2001 | Include | 4 | Jerry Bailey | Bud Delp | Brereton C. Jones | 1³/ | 1:55.61 | $750,000 | I |
| 2000 | Golden Missile | 5 | Kent Desormeaux | Joe Orseno | Frank Stronach | 1³/ | 1:54.65 | $750,000 | I |
| 1999 | Real Quiet | 4 | Gary Stevens | Bob Baffert | Michael E. Pegram | 1³/ | 1:54.31 | $750,000 | I |
| 1998 | Skip Away | 5 | Jerry Bailey | Sonny Hine | Carolyn Hine | 1³/ | 1:54.20 | $750,000 | I |
| 1997 | Gentlemen | 5 | Gary Stevens | Richard Mandella | Randall Dee Hubbard | 1³/ | 1:53.03 | $600,000 | I |
| 1996 | Star Standard | 4 | Pat Day | Nick Zito | Condren/Cornacchia | 1³/ | 1:54.40 | $600,000 | I |
| 1995 | Cigar | 5 | Jerry Bailey | William I. Mott | Allen E. Paulson | 1³/ | 1:53.60 | $600,000 | I |
| 1994 | As Indicated | 4 | Robbie Davis | Richard Schosberg | Heatherwood Farm | 1³/ | 1:55.00 | $600,000 | I |
| 1993 | Devil His Due | 4 | Herb McCauley | H. Allen Jerkens | Edith LiButti | 1³/ | 1:55.40 | $600,000 | I |
| 1992 | Strike the Gold | 4 | Craig Perret | Nick Zito | BCC Stable | 1³/ | 1:54.80 | $700,000 | I |
| 1991 | Farma Way | 4 | Gary Stevens | D. Wayne Lukas | Quarter B Farm | 1³/ | 1:52.40 | $750,000 | I |
| 1990 | Criminal Type | 5 | José Santos | D. Wayne Lukas | Calumet/J. K. Arnemann | 1³/ | 1:53.00 | $1,000,000 | I |
| 1989 | Blushing John | 4 | Angel Cordero, Jr. | Richard J. Lundy | Allen E. Paulson | 1³/ | 1:53.20 | $700,000 | II |
| 1988 | Bet Twice | 4 | Craig Perret | Warren A. Croll, Jr. | Blanche P. Levy | 1³/ | 1:54.20 | $710,000 | |
| 1959- | 1987 No Races | - | No Races | No Races | No Races | 1³/ | no races | no races | |
| 1958 | Vertex | 4 | Sam Boulmetis, Sr. | Joseph F. Piarulli | J. J. Brunetti/F. A. Piarulli | 1³/ | 2:00.60 | $60,000 | |
| 1957 | Promised Land | 3 | Bill Hartack | Hirsch Jacobs | Ethel D. Jacobs | 1³/ | 1:57.40 | $60,000 | |
| 1956 | Summer Tan | 4 | Dave Erb | Sherrill W. Ward | Mrs. J. W. Galbreath | 1³/ | 1:56.60 | $60,000 | |
| 1955 | Sailor II | 3 | Hedley Woodhouse | Preston M. Burch | Isabel Dodge Sloane | 1³/ | 1:57.60 | $66,500 | |
| 1954 | Helioscope | 3 | Sam Boulmetis, Sr. | Howard Hausner | William G. Helis, Jr. | 1³/ | 1:59.00 | $60,000 | |
| 1953 | Tom Fool | 4 | Ted Atkinson | John M. Gaver, Sr. | Greentree Stable | 1³/ | 1:55.80 | $50,000 | |
| 1952 | General Staff | 4 | Glen Lasswell | Jimmy McGee | Larry S. MacPhail | 1³/ | 1:57.40 | $41,500 | |
| 1951 | Bryan G. | 4 | Ovie Scurlock | Casey Hayes | Meadow Stable | 1³/ | 1:57.40 | $41,500 | |
| 1950 | One Hitter | 4 | Ted Atkinson | John M. Gaver, Sr. | Greentree Stable | 1³/ | 1:58.60 | $25,000 | |
| 1949 | Capot | 4 | Ted Atkinson | John M. Gaver, Sr. | Greentree Stable | 1³/ | 1:56.80 | $25,000 | |
| 1948 | Citation † | 3 | Eddie Arcaro | Horace A. Jones | Calumet Farm | 1³/ | 1:59.80 | $25,000 | |
| 1947 | Fervent | 3 | Albert Snider | Ben A. Jones | Calumet Farm | 1³/ | 1:58.40 | $41,500 | |
| 1946 | Assault | 3 | Eddie Arcaro | Max Hirsch | King Ranch | 1³/ | 1:57.00 | $41,500 | |
| 1945 | Armed | 4 | Douglas Dodson | Ben A. Jones | Calumet Farm | 1³/ | 1:58.80 | $41,500 | |
| 1944 | Twilight Tear | 3 | Douglas Dodson | Ben A. Jones | Calumet Farm | 1³/ | 1:56.60 | $41,500 | |
| 1943 | Shut Out | 4 | Eddie Arcaro | John M. Gaver, Sr. | Greentree Stable | 1³/ | 2:00.20 | $41,500 | |
| 1942 | Whirlaway † | 4 | George Woolf | Ben A. Jones | Calumet Farm | 1³/ | 2:00.40 | $16,500 | |
| 1941 | Market Wise | 3 | Wendell Eads | George W. Carroll | Louis Tufano | 1³/ | 1:58.80 | $16,500 | |
| 1940 | Challedon | 4 | George Woolf | Don Cameron | Branncastle Farm | 1³/ | 2:03.20 | $16,500 | |
| 1939 | Challedon | 3 | Eddie Arcaro | Louis J. Schaefer | Branncastle Farm | 1³/ | 1:59.00 | $16,500 | |
| 1938 | Seabiscuit | 5 | George Woolf | Tom Smith | Charles S. Howard | 1³/ | 1:56.60 | $25,000 | |
| 1937 | War Admiral | 3 | Charley Kurtsinger | George Conway | Glen Riddle Farm | 1³/ | 1:58.80 | $10,000 |
- For 3-yr-olds in 1937 and 1954.
- † Walkovers in 1942 and 1948.
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