The boxing world has always thrived on drama, but some nights leave fans stunned and pundits speechless. In the blink of an eye, a dominant champion can fall, rewriting history and reshaping legacies in ways few predict.

Upsets in the ring are more than just shocking results—they are defining moments. From underdogs defying odds to veteran fighters facing unexpected defeats, these bouts reveal the unpredictable heartbeat of the sport.

Boxing history is filled with matches where expectations were shattered. The roar of the crowd, the stunned silence and the scramble for headlines all capture why these monumental upsets and brutal fights remain etched in memory.

James Douglas vs. Mike Tyson (1990)

On February 11, 1990, Mike Tyson entered the ring as an undefeated, undisputed heavyweight

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