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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Derby has not won it as yet.
Roses
Eddie Arcaro [February 19, 1916 - November 4, 1997] is considered the best rider to have ever played at the Kentucky Derby. Specifically, Arcaro is a five-time Kentucky Derby winner. He in fact is considered the greatest jockey in American horse racing history. That honor comes from the fact of his being one of only two jockeys to win the Derby five times. But he also is the only jockey to have won the U.S. Triple Crown twice: in 1941 on Whirlaway, and in 1948 on Citation.
Issac Burns Murphy raced in the Kentucky Derby 11 times and won the event in 1884 on Buchanan, on Riley in 1890 and on Kingman in 1891. He had 1,412 starts with 628 wins which is a record that will last forever.
Chicken Wing, a man won 8,000 dollars on a outside bet.