Hollywood Park Racetrack opened its doors on June 10, 1938, and Seabiscuit, under jockey George Woolf, won the $50,000 added race's inaugural running on July 16.

The race was not run in 1942 or 1943 due to Hollywood Park being closed and used as an airplane parts storage depot during World War II.

The Hollywood Park grandstand was rebuilt and the facility reopened in time for a two-part split 1950 season.

In 1980, Mary Lou Tuck became the first woman trainer to win the Hollywood Gold Cup with Go West Young Man.

In 1999, the Blood-Horse magazine List of the Top 100 U.S. Racehorses of the 20th Century was published, and fourteen horses on the list had won the Hollywood Gold Cup: Citation, Affirmed, Round Table, Cigar, Swaps, Seabiscuit, Skip Away, Gallant Man, Challedon, Ack Ack, Native Diver, Noor, Two Lea and Exceller.

In the 73rd running of the Hollywood Gold Cup in 2012, Chantal Sutherland, aboard Game On Dude, became the first female jockey to win the race.