Winners of The Jefferson Cup Stakes Since 1999
| Year |
Winner |
Age |
Jockey |
Trainer |
Owner |
Distance (Miles) |
Time |
Grade |
| 2011 | Banned | 3 | Jose Lezcano | Tom Proctor | Glen Hill Farm | 1-1/16 | 1:43.66 | II |
| 2010 | Gleam of Hope | 3 | E. T. Baird | Anthony L. Reinstedler | Dr. A. C. & Claire Asbury | 1-1/16 | 1:45.61 | II |
| 2009 | Florentino | 3 | Alan Garcia | Kiaran McLaughlin | Darley Racing | 1-1/8 | 1:51.59 | II |
| 2008 | Tizdejavu | 3 | Garrett Gomez | Gregory Fox | Michael Cooper & Pamela Ziebarth | 1-1/8 | 1:49.15 | II |
| 2007 | Inca King | 3 | Shaun Bridgmohan | Steve Asmussen | Heiligbrodt Racing | 1-1/8 | 1:48.94 | II |
| 2006 | Brilliant | 3 | Robby Albarado | Neil J. Howard | Mill House | 1-1/8 | 1:48.47 | II |
| 2005 | Rush Bay | 3 | Robby Albarado | Thomas Amoss | Phoebe Ann Miller Trust | 1-1/8 | 1:48.75 | III |
| 2004 | Prince Arch | 3 | Brice Blanc | Kenneth McPeek | Raymond H. Cottrell, Sr. | 1-1/8 | 1:50.61 | III |
| 2003 | Senor Swinger | 3 | Robby Albarado | Bob Baffert | Bob & Beverly Lewis | 1-1/8 | 1:47.54 | III |
| 2002 | Orchard Park | 3 | Mark Guidry | William I. Mott | Peter Vegso | 1-1/8 | 1:48.53 | III |
| 2001 | Indygo Shiner | 3 | Lonnie Meche | W. Elliott Walden | Joseph LaCombe et al. | 1-1/8 | 1:48.81 | III |
| 2000 | King Cugat | 3 | Robby Albarado | William I. Mott | Centennial Farms | 1-1/8 | 1:47.27 | |
| 1999 | Special Coach | 3 | Jorge Velasquez | Bill March | Cecilia Dixon | 1-1/8 | 1:49.82 | |
| 1998 | Buff | 3 | Calvin Borel | 1-1/8 | 1:50.80 | |||
| 1997 | Greed Is Good | 3 | Willie Martinez | 1-1/8 | 1:49.47 | |||
| 1996 | Unruled | 3 | Craig Perret | 1-1/8 | 1:50.07 | |||
| 1995 | Ago | 3 | Shane Sellers | 1-1/8 | 1:49.48 | |||
| 1994 | Milt's Overyure | 3 | Pat Day | 1-1/8 | 1:48.21 |
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