Run annually, on the first Saturday in May, over a mile and a quarter at Churchill Downs in Louisville, Kentucky, the Kentucky Derby is, of course, the first leg of the American Triple Crown. The race was established in 1875 and, although contested over a mile and a half until 1896, has been run without interruption ever since. Fillies receive a 5lb weight-for-sex allowance from colts but, even so, in 149 renewals of ‘The Run for the Roses’, just three have managed to beat their male counterparts.
The first to do so was Regret on May 8, 1915. Bred and owned by Harry Whitney, trained by James Rowe Sr. and well ridden by Joseph ‘Joe’ Notter, Regret made all the running and drew clear in the closing stages to win, eased down, by two lengths. According to Martin ‘Matt’ Winn, President of Churchill Downs, the Kentucky Derby ‘needed only a victory by Regret [who was based in New York] to create for us some coast-to-coast publicity, and Regret did not fail us.’
It was not until 65 years later, on May 3, 1980, that another filly won the Kentucky Derby. The filly in question was Genuine Risk, bred and owned by Diana Firestone, trained by LeRoy Jolley and ridden by Jacinto Vásquez. Settled early, Genuine Risk made ground approaching the half-mile marker and took command in the home straight, beating Rumbo by a length. She remains the only filly to finish in the money in all three Triple Crown races, subsequently finishing second, under controversial circumstances, in the Preakness Stakes and second again in the Belmont Stakes.
Last, but by no means least, on the short list of winning fillies is Winning Colors, who enjoyed her 15 minutes – or, rather, 2 minutes and 2.2 seconds – of fame on May 7, 1988. Owned by Eugene Klein, trained by Darrell Lukas and ridden by Gary Stevens, she, too, made all the running and held on grimly close home to win by a neck. She, too, contested the Preakness Stakes and Belmont Stakes, finishing third in behind Risen Star in the former, but unplaced behind the same rival in the latter.