Technically, a mare is defined as a female horse over the age of three. A filly is a female horse three years or younger. Since the Kentucky Derby is a race for 3-year-olds only, no mare has ever won. However, three fillies have won the Kentucky Derby: Regret (1915); Genuine Risk (1980); and Winning Colors (1988).
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Three fillies that have won the Kentucky Derby. The first to do it was Regret in 1915. It would be 65 years until another filly won: Genuine Risk in 1980. The last filly to win the Derby was Winning Colors in 1988.
Regret was the first filly to win the Kentucky Derby in 1915. Genuine Risk won in 1980, and Winning Colors was the most recent in 1988.