In the spring of 1988, the large filly won the Santa Anita Derby, defeating colts her age by 7½ lengths. Sent to Churchill Downs for the Kentucky Derby, she was up against a stellar field of colts including Risen Star, Seeking the Gold, Forty Niner, Regal Classic, and co-favorite Private Terms. As was her habit, Winning Colors broke fast and raced to the lead. Although Forty Niner made a charge in the homestretch, she held him off to win by a neck.