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Oliver Lewis was born enslaved in 1856 in Woodford County, KY. Oliver won the inaugural Kentucky Derby on May 17, 1875. He set the record for the 1.5-mile race in 2 minutes and 37.75 seconds. Lewis won by two lengths in front of an estimated crowd of 10,000 spectators and in a field of 15 three-year-old horses.

Oliver, a lightweight jockey, from May to July 1875 was mounted on four Thoroughbreds of the McGrathiana Stable. He placed top two in 8 of his 9 starts that year.

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