There is Little Doubt

this poll is correct in naming Dark Star, the Kentucky Derby winner of 1953, the biggest upset winner in the history of the race.

He handed favored Native Dancer, who later won the Preakness and Belmont, his only defeat in 21 starts.

Of course, the biggest upset in racing history has to be the 1919 Sanford Stakes, where Man O'War lost for the only time in his career, and to a horse named Upset.

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