Evander Holyfield vs. Mike Tyson

Holyfield was a good boxer but he made his success and name on the back of defeating Tyson twice in his career. Tyson was favourite going into the fight and bookies had Holyfield at 25/1 on the fight night. But boy he turned it as early as the first minute of first round.

Tyson knew he is in with a surprise after the first round, Holyfield just toyed with Tyson throughout the fight and than ear biting and all that stuff.
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Corrie Sanders vs. Wladimir Klitschko

Wladimir is fighting Alex Leapai today while I am writing this list, he has been on top of his game for last decade and defending his Heavyweight boxing championship belts for the last 10 years being unbeaten. But He suffered three defeat at the peak of his career and one of them was a devastating knock-out in the hands of Corrie Sanders.

Freddi Roach claims Klitschko is the hardest puncher he has seen but Sanders had other ideas as he exposed a weak chin and loop holes in otherwise water tight defence of Klitscko. Sanders knocked down Klitschko three times in the first 2 rounds and referee stopped the fight in the middle of 2nd round.
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Hasim Rahman vs. Lennox Lewis

British heavyweight boxer Lewis was one of the best boxer in the history of boxing, certainly the most under-rated fight of all times. He had the power, was smarter in the ring and most importanly was brave (apart from taking rematch against Vitali).

Lennox was caught with a devastating right hand punch which made Lewis fall like pile bricks. It was a shocking defeat consider he would go on to beat bigger better names later in his career.
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George Foreman vs. Michael Moorer

Foreman was losing and losing convincingly upto 10th round but a sneaky tradmark right hand from foreman put Moorer to sleep.

Foreman was in the twilight of his career while Moorer was at the peak of his career and what a terror he was, winning fights with early knockouts and gave Foreman one of the worst beating of his career but a split second lose of concentration and bang lights out for Moorer.
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Mike Tyson vs. Buster Douglas

One of the greatest boxing upset and certainly the most unpredictable one in heavyweight division when at the time invincible Mike Tyson was lost against James “Buster” Douglas.

Before the fight Douglas was riding on odds of 42/1 and nobody saw it coming when he dismental Tyson in what can easily be describe as the biggest heavyweight upset.