In the beginning of a trilogy of bouts with the 25-year old Riddick Bowe, who had won a silver medal in the 1988 Olympics, in the Super Heavyweight division, he suffered his first defeat when Bowe won the undisputed title by a 12-round unanimous decision in Las Vegas. Round Ten of that bout was named the Round of the Year by Ring Magazine. Holyfield was knocked down in round 11. He made the mistake of getting into a slugfest with the younger, bigger and stronger Bowe, leading to his defeat.

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