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Horses can only enter the derby when they are at a certain age, which means that can't enter the derby more than once. So the answer is pretty much none. But they can enter the Preakness and Belmont Stakes after the Derby in the same year.

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14y ago
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16y ago

Eddie Arcaro and Bill Hartack, both with 5 a piece.

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12y ago

Only Thoroughbreds have won the Kentucky Derby because the race is only open to registered Thoroughbreds, age 3.

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13y ago

kent desormeau

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Q: What jockey has won the preakness the most times?
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