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Yes, fillies have been among the Kentucky Derby's winners! Regret [1912 - April 11, 1934] was the first filly [female horse] to win the Kentucky Derby, in 1915, with a time of 2:05.40 minutes. Genuine Risk [February 15, 1977 - August 18, 2008] was the second filly to win the Derby, in 1980, with a time of 2:02.00 minutes. Winning Colors [February 14, 1985 - February 17, 2008] was the third and final filly to win the Derby, in 1988, with a time of 2:02.20 minutes.

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Q: Has a filly ever won the Kentucky Derby?
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