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The last decade has seen a remarkable stretch of Kentucky Oaks winners, including two that went on to achieve success in the classics.
One month after her Oaks win, Rags to Riches (2007) became the first filly in more than a century to win the Belmont Stakes, the third leg of the Triple Crown.
Two weeks after her Oaks success, Rachel Alexandra (2009) ended an 85-year drought for fillies in the Preakness, the second leg of the Triple Crown. She is the only Kentucky Oaks winner ever to win a Horse of the Year title.
Oaks winners Proud Spell, Blind Luck, and Untapable also went on to be named champion three-year-old filly.
A Full List of Kentucky Oaks Winners
In 2020, Brad Cox’s Shedaresthedevil won the Kentucky Oaks in record time (1 1/8 miles in 1:48.28), making Cox a 2-time winner of the historic race. She joins the below list of illustrious Oaks winners:
| Year | Horse | Trainer | Jockey |
| 2020 | Shedaresthedevil | Brad Cox | Florent Geroux |
| 2019 | Serengeti Empress | Tom Amoss | Jose Ortiz |
| 2018 | Monomoy Girl | Brad Cox | Florent Geroux |
| 2017 | Abel Tasman | Bob Baffert | Mike E. Smith |
| 2016 | Cathryn Sophia | John C. Servis | Javier Castellano |
| 2014 | Lovely Maria | J. Larry Jones | Kerwin D. Clark |
| 2014 | Untapable | Steven M. Asmussen | Rosie Napravnik |
| 2013 | Princess of Sylmar | Todd A. Pletcher | Mike E. Smith |
| 2012 | Believe You Can | J. Larry Jones | Rosie Napravnik |
| 2011 | Plum Pretty | Bob Baffert | Martin Garcia |
| 2010 | Blind Luck | Jerry Hollendorfer | Rafael Bejarano |
| 2009 | Rachel Alexandra | Hal R. Wiggins | Calvin H. Borel |
| 2008 | Proud Spell | J. Larry Jones | Gabriel Saez |
| 2007 | Rags to Riches | Todd A. Pletcher | Garrett K. Gomez |
| 2006 | Lemons Forever | Dallas Stewart | Mark Guidry |
| 2005 | Summerly | Steven M. Asmussen | Jerry D. Bailey |
| 2004 | Ashado | Todd A. Pletcher | John R. Velazquez |
| 2003 | Bird Town | Nicholas P. Zito | Edgar S. Prado |
| 2002 | Farda Amiga | Paulo H. Lobo | Chris J. McCarron |
| 2001 | Flute | Robert J. Frankel | Jerry D. Bailey |
| 2000 | Secret Status | Neil J. Howard | Pat Day |
| 1999 | Silverbulletday | Bob Baffert | Gary L. Stevens |
| 1998 | Keeper Hill | Robert J. Frankel | David Romero Flores |
| 1997 | Blushing K. D. | Sam B. David, Jr. | Lonnie Meche |
| 1996 | Pike Place Dancer | Jerry Hollendorfer | Corey S. Nakatani |
| 1995 | Gal in a Ruckus | John T. Ward, Jr. | Herb McCauley |
| 1994 | Sardula | Brian A. Mayberry | Eddie J. Delahoussaye |
| 1993 | Dispute | Claude R. McGaughey III | Jerry D. Bailey |
| 1992 | Luv Me Luv Me Not | Glenn S. Wismer | Fabio A. Arguello, Jr. |
| 1991 | Lite Light | Jerry Hollendorfer | Corey S. Nakatani |
| 1990 | Seaside Attraction | D. Wayne Lukas | Chris J. McCarron |
| 1989 | Open Mind | D. Wayne Lukas | Angel Cordero, Jr. |
| 1988 | Goodbye Halo | Charles E. Whittingham | Pat Day |
| 1987 | Buryyourbelief | Lazaro S. Barrera | Jose A. Santos |
| 1986 | Tiffany Lass | Lazaro S. Barrera | Gary L. Stevens |
| 1985 | Fran’s Valentine | Joseph Manzi | Patrick A. Valenzuela |
| 1984 | Lucky Lucky Lucky | D. Wayne Lukas | Angel Cordero, Jr. |
| 1983 | Princess Rooney | Frank Gomez | Jacinto Vasquez |
| 1982 | Blush With Pride | D. Wayne Lukas | William Shoemaker |
| 1981 | Heavenly Cause | Woodford C. Stephens | Laffit A. Pincay, Jr. |
| 1980 | Bold ‘n Determined | Neil D. Drysdale | Eddie J. Delahoussaye |
| 1979 | Davona Dale | John M. Veitch | Jorge Velasquez |
| 1978 | White Star Line | Woodford C. Stephens | Eddie Maple |
| 1977 | Sweet Alliance | Grover G. Delp | Chris J. McCarron |
| 1976 | Optimistic Gal | LeRoy S. Jolley | Braulio Baeza |