Electric sheep site, TheUppercutTV, presents: The three biggest upsets in the history of boxing fights

There’s almost nothing better than a major upset in a boxing match. Unless you had money on the sure thing – in which case, you know, then there’s plenty that’s better than an upset in a boxing match. But to the impartial observer or the gambler with money on the underdog, there really is nothing quite like seeing a heavily favored champ go down after ten good rounds.

What follows is our top three biggest upsets in the history of boxing fights. Feel free to disagree with any of our choices or omissions, but we think you’ll have to admit, these were some pretty big ones.

Randy Turpin vs. Sugar Ray Robinson, 1951

If you were to ask 10 non-boxing fans who won the fight between Randy Turpin and Sugar Ray Robinson in 1951, 10 out of 10 of them would say it was Sugar Ray Robinson. Quite possibly the greatest boxer of all time, that’s the kind of legacy he left. And yet, it was Brit boxer Randy Turpin taking it to Sugar Ray Robinson for the win in 15 rounds to claim the world middleweight title. That title belonged to Turpin for a total of three months, until Sugar Ray reclaimed it in a rematch. Turpin and Sugar Ray went ten rounds in the rematch, until Sugar Ray unleashed a series of punches so vicious on an on-the-ropes Turpin that prompted the referee to stop the match.

Cassius Clay vs. Sonny Liston, 1964

We had to include this in the list of the biggest upsets in the history of boxing fights. We did, we had to. You have to keep in mind that in 1964, Sonny Liston was considered virtually invincible, a man without equal that dispatched of champion boxers like they were flies he had to flick off his shoulder. The 22-year-old Cassius Clay went into this bout with 8-1 odds against him … and proceeded to gain the TKO over Liston in six rounds. Cassius Clay, of course, went on to be better known by the name he adopted when he converted to Islam: Muhammad Ali. Maybe not such an upset in hindsight but at the time, we assure you, this was a wild one.

Buster Douglas vs. Mike Tyson, 1990

Forget boxing fights, this is quite possibly the biggest upset in the history of sports. If hindsight is 20/20 in the case of Cassius Clay vs. Sonny Liston, then it’s something even better than 20/20 in the case of Douglas vs. Tyson. In 1990 Tyson’s entire life was in disarray. He was in the midst of a very public divorce, had legal troubles, business troubles, had just fired his long-time trainer, and was reportedly spending less and less time in the gym. And yet, the odds of James ‘Buster’ Douglas winning were 42-1. Oh to have made that bet. The bout ended in ten rounds with an out-of-it Mike Tyson on the mat searching for his mouthpiece and Buster Douglas’s arm in the air.