#5: 42 to 1 Match – 1990
In 1990, few gave Buster Douglas a chance. Facing the fearsome and undefeated Mike Tyson in Tokyo, Douglas entered the ring as a 42-to-1 underdog. Yet in one of the most stunning moments in sports history, he outboxed Tyson with heart and precision, ultimately knocking him out in the 10th round.
The world watched in disbelief as the seemingly invincible champion fell. Douglas’s triumph wasn’t just an upset—it became a defining symbol of resilience, grit, and the beautiful unpredictability that makes boxing unforgettable.
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