He was beaten 6 times in total. Gene Tunney (twice) Willie Meehan (twice) "Fireman" Jim Flynn and Jack Downey.
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Jack Dempsey was defeated by Gene Tunney in 1926. Tunney also won the 1927 rematch, though there was some controversy about the refereeing.
Tunney won both fights, and it's believed Dempsey only won one round out of the 20 they fought in total. That was in the second fight when Jack floored Tunney in the famous Long Count.