1950
Spring meeting - The box seat area was rebuilt, with the wooden construction being replaced by steel, aluminum and concrete.
1951
Guy A. Huguelet was elected Keeneland Association president, a position he held through 1955.
1953
Fall meeting - Keeneland enlarged and extended its grandstand, added 1,542 seats and increased the structure's capacity, including boxes to 3,849. A new feature of the grandstand was a dining room with a capacity of 384. Also, the finish line was moved 184 feet closer to the first turn. Moving the finish line meant that the stretch run was lengthened from 990 to 1,174 feet and that the Headley Course, formerly 40 feet shorter than a half-mile, was increased to four furlongs and 152 feet. In addition, the finish line made possible the Beard Course of seven furlongs and 184 feet.
1954
May 14
Work first began on a five-furlong training track.
1955
In September, the training track was opened.
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.
Nashua, the 1955 Horse of the Year, galloped at Keeneland in his final public appearance prior to going to stud at Spendthrift Farm.
Keeneland held the inaugural running of the Spinster Stakes.