The Cheltenham Gold Cup, over 3 ¼ miles, was run for the first time in 1924, with the Champion Hurdle following in 1927.

[1] The course's most prestigious meeting is the Cheltenham Festival, held in March, which features several Grade I races including the Cheltenham Gold Cup, Champion Hurdle, Queen Mother Champion Chase, Ryanair Chase and the Stayers' Hurdle.

The Old Course is the racecourse used for The Showcase, The November Meeting and the first two days of the Cheltenham Festival.

The University of Gloucestershire holds its graduation ceremony and summer ball at the racecourse.

In 2001 during the 2001 United Kingdom foot-and-mouth outbreak, the 2001 Cheltenham Festival was cancelled for the first time since 1943 due to World War II.

In 2015, Cheltenham Racecourse opened the £45m 6,500-capacity Princess Royal Stand,[3] which completed the redevelopment of the course.