- 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 |
| 1875 | Vinaigrette | J. Houston, 97 | A. B. Lewis & Co. | N/A | Gyptis, 97 | Elemi, 97 | $1,175 | 2:39 3/4 | |
| 1876 | Necy Hale | W. James, 97 | F. B. Harper | N/A | Plenty, 97 | Lady Clipper, 97 | 1,900 | 2:42 1/2 | |
| 1877 | Felicia | W. James, 97 | J. W. Reynolds | N/A | Bradamante, 97 | Aunt Betsy, 97 | 2,550 | 2:39 | |
| 1878 | Belle of Nelson | Booth, 97 | Mattingly & Co. | N/A | Buena Vista, 97 | Fortuna, 97 | 2,650 | 2:39 | |
| 1879 | Liahtunah | Hightower, 97 | J. A. Grinstead | N/A | Ada Glenn, 97 | Buckden Lass, 97 | 3,350 | 2:40 1/4 | |
| 1880 | Longitude | J. McLaughlin, 102 | J. G. Malone | N/A | Bye and Bye, 102 | Ersilia, 102 | 3,250 | 2:41 3/4 | |
| 1881 | Lucy May | Wolfe, 102 | R. F. Johnson | N/A | Belle of the Highlands, 102 | Mrs. Chubbs, 102 | 3,000 | 2:41 | |
| 1882 | Katie Creel | J. Stoval, 102 | Johnson & Co. | C. A. Johnson | Pinafore, 102 | Issie, 102 | 3,240 | 2:39 | |
| 1883 | Vera | J. Stoval, 102 | R. C. Pate | J. Pate | Orange Blossom, 102 | Billetta, 102 | 3,220 | 2:39 3/4 | |
| 1884 | Modesty | I. Murphy, 105 | Ed Corrigan | E. Corrigan | Highflight, 105 | Bluette, 105 | 3,030 | 2:48 1/4 | |
| 1885 | Lizzie Dwyer | Fuller, 105 | Ed Corrigan | E. Corrigan | Constellation, 105 | Exile, 105 | 3,800 | 2:40 3/4 | |
| 1886 | Pure Rye | E. Garrison, 113 | Melbourne Stable | N/A | Red Girl, 113 | Ada D., 113 | 4,170 | 2:41 | |
| 1887 | Florimore | Johnston, 113 | T. H. Stevens | D. W. Kelly | Wary, 113 | Bannail, 113 | 3,330 | 2:40 3/4 | |
| 1888 | Ten Penny | A. McCarthy, Jr., 113 | M. Welsh | N/A | Los Angeles, 114 | Quindaro Bell, 113.5 | 3,770 | 2:42 | |
| 1889 | Jewel Ban | J. Stoval, 113 | J. T. Clay | W. Clay | Bandolette, 113 | Retrieve, 113 | 3,850 | 2:41 | |
| 1890 | English Lady | Hollis, 113 | Scoggan Bros. | N/A | Marie K.*, 113 | 3,610 | 2:42 1/2 | ||
| 1891 | Miss Hawkins | T. Britton, 117 | Talbot Bros. | H. J. Talbot | Ethel, 117 | Bonnie Bird, 117 | 3,860 | 2:18 1/4 | |
| 1892 | Miss Dixie | H. Ray, 117 | Col. J. E. Pepper | M. Danaher | Unadilla, 117 | Greenwich, 117 | 3,470 | 2:14 1/4 | |
| 1893 | Monrovia | J. Reagan, 117 | Ed Brown | Ed Brown | Elizabeth L., 117 | Joanna, 117 | 2,780 | 2:16 | |
| 1894 | Selika | A. Clayton, 117 | Bashford Manor | J. H. Morris | Charity, 117 | Shuttle, 117 | 2,600 | 2:15 | |
| 1895 | Voladora | A. Clayton, 117 | Pastime Stable | N/A | Alabama, 117 | Kathryn, 117 | 1,830 | 2:16 3/4 | |
| 1896 | Souffle | C. Thorpe, 112 | J. M. Murphy | J. Healy | Myrtle Harkness, 112 | La Gascoyne, 112 | 2,860 | 1:54 1/2 | |
| 1897 | White Frost | T. Burns, 112 | E. S. Gardner & Son | L. C. Davis | Rosinante, 112 | Taluca, 112 | 2,410 | 1:49 | |
| 1898 | Crocket | J. Hill, 112 | J. C. Cahn | L. Cahn | Lennep, 112 | Alleviate, 112 | 2,860 | 1:51 1/2 | |
| 1899 | Rush | J. Hill, 112 | T. C. McDowell | T. C. McDowell | May Hempstead, 117 | The Lady in Blue, 112 | 2,410 | 1:52 1/2 | |
| 1900 | Etta | M. Overton, 112 | Ed Brown & Co. | Ed Brown | Scarlet Lily, 112 | Cleora, 112 | 2,410 | 1:48 |
| 1875-1900 | 1901-1925 | 1926-1950 | 1951-1975 | 1976-2000 | 2001-2005|