Winners of The Kentucky Cup Classic Stakes
| Year |
Winner |
Age |
Jockey |
Trainer |
Owner |
Time |
| 2011 | Future Prospect | 7 | Edgar Prado | Dodson Skaggs | Dodson Skaggs | 1:44.71 |
| 2010 | No Race | |||||
| 2009 | Furthest Land | 4 | Garrett Gomez | Michael J. Maker | Ken & Sarah Ramsey | 1:48.41 |
| 2008 | Zanjero | 4 | Shaun Bridgmohan | Steve Asmussen | Winchell Thoroughbreds | 1:49.27 |
| 2007 | Hard Spun | 3 | Mario Pino | J. Larry Jones | Fox Hill Farms | 1:48.48 |
| 2006 | Ball Four | 5 | Willie Martinez | Patrick L. Biancone | M. Tabor / D. Smith | 1:48.29 |
| 2005 | Shaniko | 4 | Rafael Bejarano | Todd A. Pletcher | Aaron & Marie Jones | 1:49.74 |
| 2004 | Roses in May | 3 | John R. Velazquez | Dale L. Romans | Ken & Sarah Ramsey | 1:49.13 |
| 2003 | Perfect Drift | 4 | Pat Day | Murray W. Johnson | Stonecrest Farm | 1:50.43 |
| 2002 | Pure Prize | 4 | Mike E. Smith | C. R. McGaughey III | Ogden Mills Phipps et al. | 1:51.24 |
| 2001 | Guided Tour | 5 | Larry Melancon | Niall O'Callaghan | Morton Fink | 1:47.90 |
| 2000 | Captain Steve | 3 | Shane Sellers | Bob Baffert | Michael E. Pegram | 1:49.95 |
| 1999 | Da Devil | 4 | Calvin Borel | Forrest Kaelin | Hall, Case, Glasscock et al. | 1:50.54 |
| 1998 | Silver Charm (DH) | 4 | Gary L. Stevens | Bob Baffert | Bob & Beverly Lewis | 1:47.48 |
| 1998 | Wild Rush (DH) | 4 | Pat Day | Patrick B. Byrne | Stronach Stables | 1:47.48 |
| 1997 | Semoran | 4 | Kent Desormeaux | Bob Baffert | Donald R. Dizney | 1:48.08 |
| 1996 | Atticus | 4 | Corey Nakatani | Richard Mandella | La Presle Farm | 1:47.43 |
| 1995 | Thunder Gulch | 3 | Gary L. Stevens | D. Wayne Lukas | Michael Tabor | 1:49.42 |
| 1994 | Tabasco Cat | 3 | Pat Day | D. Wayne Lukas | Overbrook / D. P. Reynolds | 1:50.32 |
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