Part of the 1936 inaugural events for the new Keeneland Race Course, the first two editions of the Ashland Stakes were open to fillies and mares, 3-years of age and older.[1] Not run again until 1940, it was then made a race exclusively for 3-year-old fillies. During World War II, from 1943 through 1945 the race was hosted by Churchill Downs in Louisville.
The Ashland Stakes was run in two heats in 1952, 1965, 1974 and 1980. Don Brumfield is the only jockey to ever have won both heats. In the 1974 edition, Brumfield rode to victory on Winged Wishes, a horse owned by his mother, Viola, then took the second running aboard Darby Dan Farm's, Maud Muller.
Since its inception, the Ashland Stakes has been raced at various distances:
1936–1937, 1981 to present : 1+1⁄16 miles
1940–1973 : 6 furlongs
1974–1980 : 7 furlongs, 184 feet
In 2014, the Ashland finished in a Dead heat between Rosalind and Room Service.