- Oaks Day First Race Post Time: 11:00 a.m. ET, Gates Open at 8:00 a.m.
- Visit The Oaks' Companion Website at www.kentuckyderby.com
- Oaks Future Wager Pool 3 Final Odds
- Kentucky Oaks Post Time: May 4, 5:45 p.m. ET Race 10
| 1875-1900 | 1901-1925 | 1926-1950 | 1951-1975 | 1976-2000 | 2001-2005|
| Year | Winner | Jockey, WT. | Owner | Trainer | second, Wt. | third, Wt. | Val. win | Time | Track |
| 1901 | Lady Schorr | J. Woods, 117 | J. W. Schorr | J. W. Schorr | Isobel, 112 | Edith Q., 112 | 2,410 | 1:53 | |
| 1902 | Wainamoinen | M. Coburn, 112 | Talbot Bros. | H. J. Talbot | Marque, 112 | Autumn Leaves, 112 | 2,410 | 1:51 1/4 | |
| 1903 | Lemco | J. Reiff, 112 | Ed Corrigan | F. Kelly | Mary Lavana, 112 | The Crisis, 112 | 2,410 | 1:49 3/4 | |
| 1904 | Audience | G. Helgeson, 117 | S. S. Brown | H. C. Riddle | Outcome, 112 | White Plume, 112 | 2,410 | 1:51 | |
| 1905 | Janeta | D. Austin, 112 | Cassin & Rogers | R. L. Rogers | Mum, 112 | Sis Lee, 112 | 2,410 | 1:49 3/4 | |
| 1906 | King’s Daughter | E. Robinson, 112 | T. C. McDowell | T. C. McDowell | Lady Navarre, 117 | Lady Anne, 112 | 2,410 | 1:47 4/5 | |
| 1907 | Wing Ting | J. Lee, 112 | J. S. Hawkins | J. S. Hawkins | Altuda, 112 | Little Turner, 112 | 2,410 | 1:50 1/5 | |
| 1908 | Ellen-a-Dale | V. Powers, 105 | T. C. McDowell | Geo. Denny | Boema, 112 | Estrada, 105 | 2,410 | 1:46 3/5 | |
| 1909 | Floreal | Heidel, 112 | W. H. Fizer | W. H. Fizer | Pink Wings, 105 | Cordova, 112 | 2,410 | 1:49 1/5 | |
| 1910 | Samaria | R. Scoville, 112 | J. P. Ross & Co. | W. McDaniel | Foxy Mary, 112 | My Gal, 112 | 1,910 | 1:50 1/5 | |
| 1911 | Bettie Sue | T. Rice, 112 | A. Brown | D. Huestis | Princess Callaway, 112 | Iima, 112 | 1,910 | 1:48 | |
| 1912 | Flamma | J. Butwell, 112 | E. F. Condran | J. Duffy | Floral Day, 112 | Beautiful, 105 | 1,910 | 1:51 1/5 | |
| 1913 | Cream | C. Ganz, 112 | C. C. Van Meter | A. Baker | Floral Park, 112 | Gowell, 117 | 1,950 | 1:47 3/5 | |
| 1914 | Bronzewing | W. Obert, 117 | A. P. Humphrey, Jr. | D. Lehan | Casuarina, 112 | Bracktown Belle, 112 | 2,320 | 1:45 3/5 | |
| 1915 | Waterblossom | E. Martin, 117 | T. C. McDowell | Geo. Denny | One Step, 112 | Lady Rotha, 112 | 2,530 | 1:46 3/5 | |
| 1916 | Kathleen | R. Goose, 112 | Geo. J. Long | Pete Coyne | Mandy Hamilton, 117 | Lady Always, 112 | 2,410 | 1:47 2/5 | |
| 1917 | Sunbonnett | J. Loftus, 112 | A. K. Macomber | B. W. Jennings | Diamond, 112 | Battle, 112 | 3,035 | 1:46 4/5 | |
| 1918 | Viva America | W. Warrington, 112 | C. T. Worthington | W. N. Potts | Fern Handley, 112 | Mistress Polly, 112 | 2,580 | 1:46 4/5 | |
| 1919 | Lillian Shaw | T. Murray, 117 | J. R. Livingston | J. McCormick | Milkmaid, 117 | Dancing Spray, 112 | 4,190 | 1:45 | |
| 1920 | Lorraine | D. Connelly, 116 | J. N. Camden | J. C. Milam | Truly Rural, 116 | Dresden, 116 | 5,470 | 1:58 2/5 | |
| 1921 | Nancy Lee | L. McAtee, 116 | P. A. Clark | J. McCormick | Prudery, 116 | Lady Madcap, 116 | 8,980 | 1:50 2/5 | |
| 1922 | Startle | D. Connelly, 116 | H. H. Hewitt | J. I. Smith | Martha Fallon, 116 | Precious Lula, 116 | 9,920 | 1:52 3/5 | |
| 1923 | Untidy | J. Corcoran, 116 | Mrs. Payne Whitney | S. P. Harlan | Sweetheart, 116 | Gadfly, 121 | 10,060 | 1:53 | |
| 1924 | Princess Doreen** | H. Stutts, 116 | Audley Farm Stable | S. M. Henderson | Nellie Morse, 121 | Befuddle, 116 | 10,160 | 1:51 4/5 | |
| 1925 | Deeming | J. McCoy, 116 | C. B. Dailey | C. B. Dailey | Buckwheat Cake, 116 | Little Visitor, 121 | 10,280 | 1:54 |
| 1875-1900 | 1901-1925 | 1926-1950 | 1951-1975 | 1976-2000 | 2001-2005|