#8
Tyson vs. Douglas (1990)
Buster Douglas's stunning tenth-round knockout of Mike Tyson in Tokyo in 1990 remains one of the most significant upsets in boxing history. Douglas entered the fight as a 42-to-1 underdog, facing the then-undefeated lineal, WBC, WBA, and IBF heavyweight champion. Despite being knocked down in the eighth round, Douglas recovered to deliver a devastating uppercut-left hook combination that ended Tyson's reign. This victory is etched in boxing lore as a monumental triumph against overwhelming odds.
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