<P> Her sire, Caro, was a top - class performer (rated 133 by Timeform), whose wins included the Poule d'Essai des Poulains, Prix Ganay and Prix d'Ispahan, before becoming a very successful breeding stallion . Caro's other progeny included Madelia, Crystal Palace, Cozzene Theia and Siberian Express . Winning Colors dam, All Rainbows won seven races and finished third in the Delaware Oaks. and was also a half - sister to Chris Evert . </P> <P> Racing on the West Coast of the United States for trainer D. Wayne Lukas, Winning Colors won both of her starts at age two . </P> <P> In the spring of 1988, the large filly won the Santa Anita Derby, defeating colts her age by 71⁄2 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 . </P> <P> In the Preakness Stakes, the second leg of the U.S. Triple Crown, Winning Colors finished third to Risen Star, who then won the 11⁄2 mile Belmont Stakes by fifteen lengths while Winning Colors finished out of the money . </P>

When did winning colors win the kentucky derby