Keeneland held its inaugural meet October 15th 1936. The nine day meeting drew over 25,000 fans.
In 1956 Louis Lee Haggin II was elected Keeneland Association president, a position he held to 1970. Duval A. Headley was elected Keeneland Race Course president. Between the spring and fall meetings, the main track was completely overhauled at a cost of $150,000.
This project was designed to improve surface and sub-surface drainage. In 1971 The Blue Grass Stakes marked the first million-dollar day of wagering in Keeneland’s history – $1,052,866. In 1984 the first phase of a $3-million construction project was completed before the spring meeting. Sixteen new saddling stalls were built in the paddock during the winter, and preliminary work was started on a 40,000-square-foot addition to the rear of the grandstand. Half of the old saddling stalls were demolished following the 1983 fall meeting, and new stalls were constructed in a semi-circle at the west end of the paddock. Keeneland began a $2.7-million construction project that would be completed in early 1986, the year the track celebrated its 50th anniversary. The 1997 November Breeding Stock Sale set an industry record for gross sales–$213 million.
In 1997 former President George Bush attended the races as the guest of W.S. Farish, the owner of Lane’s End Farm, and presented the trophy to the owners of Favorite Trick after the undefeated colt romped to victory in the Lane’s End Breeders’ Futurity. It marked the first time that a former President of the United States had made a trophy presentation at Keeneland. Total wagering topped $100 million for the first time during the 16-day spring meeting. In 1998 a $5.8 million renovation of the west end of the grandstand is completed in time for the fall meeting.