Biggest Upsets in Boxing History: Shocking Moments in the Ring

Many of us like an underdog, and in the boxing ring, when the pressure is on, there are many possible outcomes. Nobody is ever a dead certainty for a fight, even if it looks to be the case beforehand.

Over the years, we’ve seen some boxers look like dead certs and not manage to get the job done, with some outsiders that shocked the world, and etched their names into the annals of boxing lore. We use the term “puncher’s chance” in boxing, meaning that there’s always a chance so long as somebody can throw a punch…

What Makes a Favorite?

There’s usually a favorite in boxing, dictated by the bookmakers and the form. Loads of factors go into how people think of a fight before it happens. Fight records are key to this, if somebody is 39-0 and has never lost a fight, it is likely that they will be the favorite.

The odds dictate whether somebody is a favorite or not, and the betting sites set the odds, but they can be tracked live via Thunderpick Sportsbook as this shows odds moving beforehand. Odds are impacted by lots of different things and there are often movements before the fights. If a fighter looks out of shape at the weigh-in, for instance, this could mean an influx of bets for the opponent and change the odds totally.

The peril in boxing makes for an interesting dance between the fighters, and the most skilled and prepared fighters can have an off night, or their opponents can rise to the occasion, delivering a performance that defies expectations. Once Michael Buffer says it’s time and the bell rings there is really no telling what is going to happen.

Muhammad Ali vs. George Foreman (1974)

Ali transcended the sport, and the “Rumble in the Jungle” is something that even non-boxing fans have heard about – an iconic bout that featured an upset. Before his grilling days, George Foreman was the reigning heavyweight champion and had a reputation for his punching power. Though Muhammad Ali was a legend and former champion, he was seen as past his prime and was not expected to withstand Foreman.

Ali lived up to his claim of stinging like a bee when he implemented a brilliant strategy, rope-a-dope, something boxers now regularly try to do themselves, the process involved allowing Foreman to tire himself out by throwing punches while Ali leaned against the ropes, conserving his energy. Eventually, he’d strike and seize the moment, knocking out Foreman and reclaiming the heavyweight title. Boxing’s GOAT was back, and this solidified Ali’s legacy and showcased his tactical genius.

Andy Ruiz Jr. vs. Anthony Joshua (2019)

A more recent major upset saw Mexican Andy Ruiz Jr. face Anthony Joshua on June 1, 2019. Media darling Joshua was the unified heavyweight champion and had a towering figure and perfect record at the time while Ruiz was considered an unlikely challenger with a less-than-impressive physique. Ruiz was the type of fighter a lot of people in boxing refer to as having a “soft body” and wasn’t fancied by the bookies, but there’s that “puncher’s chance” again.

Promotor Eddie Hearn was looking for any fighter by the end of the process of making the fight, as American contender Jarrell Miller was supposed to fight AJ but was suspended following a failed drug test. Mexico’s brightest star stepped up, and Ruiz defied expectations by knocking Joshua down multiple times before the fight was stopped in the seventh round. Joshua’s footwork had let him down, which is something we don’t usually say about the Englishman who works hard at this aspect of his fighting.

Ruiz’s victory did bring about a rematch which went more like people would have expected. Ruiz will always be able to say he was Heavyweight champ, though.

Buster Douglas vs. Mike Tyson (1990)

Tyson is still an iconic figure and makes headlines today – but in the early 90s, James “Buster” Douglas faced off against the seemingly invincible champ – Tyson, the undisputed heavyweight champion, was in his prime and destroyed every opponent put in front of him, so a 42-to-1 underdog (Douglas) didn’t look like he’d be up to the challenge.

Nothing’s a given in fighting, and in a stunning turn of events, Douglas not only survived Tyson’s attack but managed to dominate the fight and eventually floored Tyson in the 10th – the referee counted Tyson out, and Buster Douglas was declared the new heavyweight champion, this might just be the top upset out there and one of the biggest sports upsets (let alone just boxing).


Red corner or blue corner, there’s always a fine balance and there’s always a chance – when a much-fancied favorite takes on a serious outsider or someone who is considered washed up, it is still possible that one punch can change everything and suddenly the fight is over. 

Upsets are a part of the sport of boxing and are something that keeps people guessing even in fights that look like they’re destined to go one way and one way only. These are some of the most iconic upsets.

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