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36 Running on Sunday, January 31, 2021
The Jimmy Winkfield is named for James Winkfield, the last black jockey to win the Kentucky Derby. He won it twice: with His Eminence in 1901 and with Alan-a-Dale in 1902. This race was formerly known as the Best Turn from 1985 to 2004.
$100,000.00 7 Furlongs (Dirt) Grade:
| Year | Horse | Age | Weight | Time | Owner | Trainer | Jockey | Value |
|---|---|---|---|---|---|---|---|---|
| 2021 | Hello Hot Rod | 3 | 120 | 1:26.30 | Russell, Brittany T. and Dark Horse Racing LLC | Brittany Russell | Trevor McCarthy | 100,000 |
| 2020 | Montauk Traffic | 3 | 118 | 1:25.64 | Chris Fountoukis | Linda Rice | Jose Lezcano | $82,500 |
| 2019 | Haikal | 3 | 118 | 1:25.24 | Shadwell Stable | Kiaran P. McLaughlin | Rajiv Maragh | $82,500 |
| 2018 | A Different Style | 3 | 122 | 1:26.07 | Fletcher & Carolyn Gray | John C. Servis | Kendrick Carmouche | $90,000 |
| 2017 | Caledonian | 3 | 122 | 1:12.19 | Curragh Stables | John Terranova | Eric Cancel | $60,000 |
| 2016 | Awesome Gent | - | 118 | 1:10:60 | Burning Sands Stable LLC | Todd Pletcher | Manuel Franco | $75,000 |
| 2015 | Ackeret | - | 118 | 1:11:13 | Pick Six Racing (David Wilkenfeld) and Silver Streak Stables | Gustavo Rodriguez | Jose L. Ortiz | $60,000 |
| 2014 | Hot Heir Skier | 3 | 116 | 1:11.25 | New Farm | Benjamin W. Perkins, Jr. | Jose L. Ortiz | $60,000 |
| 2013 | Clawback | 3 | 116 | 1:09.75 | Klaravich Stables, Inc. and Lawrence, William H. | Richard A. Violette, Jr. | Irad Ortiz, Jr. | $45,000 |
| 2012 | King and Crusader | - | 118 | 1:11.72 | James A. Riccio | Richard E. Dutrow, Jr. | Cornelio H. Velasquez | $45,000 |
| 2011 | Fort Hughes | - | 116 | 1:08.33 | Darley Stable | Kiaran McLaughlin | Eddie Castro | $39,000 |
| 2010 | Deputy Daney | - | 116 | 1:11.83 | Matthew Hand | Cathal Lynch | Angel Arroyo | $39,000 |
| 2009 | Taqarub | - | 116 | 1:09.26 | Shadwell Stable | Kiaran McLaughlin | Alan Garcia | $42,027 |
| 2008 | Go Go Shoot | - | 116 | 1:11.18 | Robert E. Hurley | James Ryerson | Alan Garcia | $49,035 |
| 2007 | Bill Place | - | 116 | 1:10.44 | Dubb, Goldfarb, et al. | Anthony Dutrow | Ramon Dominguez | $41,388 |
| 2006 | Strummer | - | 116 | 1:11.04 | Edward C. Behringer and Thomas Murray | Thomas M. Bush | Norberto Arroyo Jr. | $42,081 |
| 2005 | Maddy's Lion | - | 116 | 1:11 2/5 | Dennis J. Federico | John Pregman, Jr. | Pablo Fragoso | $48,240 |
| 2004 | Redskin Warrior | - | 116 | 1:09 4/5 | Paraneck Stable | Jennifer Pedersen | Richard Migliore | $49,095 |
| 2003 | Second in Command | - | 116 | 1:10 3/5 | Richard L. Golden | Linda Rice | Jean-Luc Samyn | $49,680 |
| 2002 | Smooth Jazz | - | 116 | 1:10 3/5 | Anthony W. Dutrow | Anthony W. Dutrow | Mario Pino | $49,770 |
| 2001 | Put It Back | - | 116 | 1:09 | Hobeau Farm | James Jerkens | N. Wynter | $48,585 |
| 2000 | Max's Pal | - | 122 | 1:10 3/5 | Raymond Dweck | Ben Perkins Jr. | Dale Beckner | $49,425 |
| 1999 | Badge | - | 115 | 1:10 1/5 | Southbelle Stable | Joseph Aquilino | Shaun Bridgmohan | $39,420 |
| 1998 | Spicy Award | - | 115 | 1:10 2/5 | Sabine Stable | Robert Barbara | Aaron Gryder | $39,852 |
| 1997 | American Champ | - | 117 | 1:10 2/5 | Arthur Appleton | Robert Camac | Anthony Black | $39,988 |
| 1996 | Romano Gucci | - | 115 | 1:10 1/5 | Herbert Kushner | Richard E. Dutrow | Richard Migliore | $48,480 |
| 1995 | Da Hoss | - | 117 | 1:11 1/5 | Prestwood Farm | Mike W. Dickinson | Mike Luzzi | $50,040 |
| 1994 | Rizzi | - | 117 | 1:09 1/5 | Hobeau Farm | H. Allen Jerkens | Jean-Luc Samyn | $48,765 |
| 1993 | Farmonthefreeway | - | 119 | 1:08 4/5 | Very Un Stable | Richard O'Connell | Richard Migliore | $53,280 |
| 1992 | Belong To Me | - | 115 | 1:09 1/5 | Middletown Stable | H. Allen Jerkens | David Lidberg | $51,930 |
| 1991 | Dodge | - | 115 | 1:09 2/5 | William T. Young | D. Wayne Lukas | Chris Antley | $52,560 |
| 1990 | For Really | - | 115 | 1:10 3/5 | Regal Oak Farm | Richard E. Dutrow | Chris Antley | $52,110 |
| 1989 | Texian | - | 115 | 1:12 2/5 | Lloyd R. French Jr. | D. Wayne Lukas | Chris Antley | $51,480 |
| 1988 | Notebook | - | 122 | 1:09 2/5 | Eugene V. Klein | D. Wayne Lukas | Jose Santos | $51,480 |
| 1987 | Java Gold | - | 119 | 1:09 2/5 | Rokeby Stable | MacK. Miller | Randy Romero | $52,700 |
| 1986 | Landing Plot | - | 115 | 1:11 | Triad Stable | Harry Wendel | J. C. Estrada | $31,860 |
| 1985 | Clever Champ | - | 119 | 1:11 2/5 | Robert S. Siegel | Richard Weiss | Richard Migliore | $33,060 |
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