Hollywood Park staged its inaugural race card on June 10, 1938. Jack Warner of the Warner Brothers film corporation was its first board chairman; Hollywood Parks original shareholders also included Al Jolson, Bing Crosby, and Walt Disney. Citation's victory in the 1951 Hollywood Gold Cup made him the first horse to earn $1 million during his race career. while Affirmed's victory in the 1979 Gold Cup made him the first horse to achieve career earnings of $2 million, and John Henry's victory in the 1983 Hollywood Turf Course made him the first horse to achieve career earnings of $4 million. From 1953-`67, Hall of Fame jockey Bill Shoemaker won 18 Hollywood riding titles. The Shoe also registered 280 career stakes wins at the Inglewood track. Hall of Fame trainer Charlie Whittingham won the Gold Cup eight times. On November 10, 1984, Hollywood hosted the inaugural Breeders Cup Championship.

Laffit Pincay Jr. reached racing's summit at Hollywood Park on Dec. 10, 1999, riding Irish Nip to victory in the sixth race. It was career win No. 8,834, one more than Bill Shoemaker, who retired with 8,833 wins in 1990. Pincay tied Shoemaker's mark on Dec. 9, rallying I Be Casual to victory in the fourth race. In addition to becoming the world’s winningest rider, Pincay rode 32 winners at the 1999 Autumn Meeting to earn his first riding title since the 1991 Spring/Summer Meeting. He finished four wins ahead of Patrick Valenzuela while claiming his 38th riding championship.