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The biggest underdog wins in boxing

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Any sport where it’s just one man up against another is going to have more exciting upsets than a team sport. People become more emotionally invested in the underdog when he’s alone in the ring and all the smart money says he’s about to get knocked around pretty badly.

Even tomato cans who make their careers by standing up to get knocked down by the title hopefuls on their way to the top have their fans who live in hope that one day they’ll beat the odds and win. 

Betting has been closely associated with boxing since it became a professional sport. This is partly because of how much mystery there is around up and coming fighters — unless you’ve been to tons of amateur fights, young fighters are unknown quantities.

Betting on a young fighter who’s an underdog can be a huge risk, but it’s one that can pay out well if it comes through. Before you bet, check the odds to find the best bookmaker for you. Finding a trustworthy bookmaker for betting on boxing is easier than ever with online betting.

Almost all the biggest boxing stars have been underdogs at some point in their careers or have lost to an underdog. Here are some of our top picks for the biggest underdog wins in boxing.

Buster Douglas vs Mike Tyson (1990)

When Buster Douglas stepped into the ring to face Mike Tyson, no one was expecting him to walk back out at the end of the fight as the WBA, WBC and IBF heavyweight champion, but that’s exactly what happened. The fight is considered one of the biggest upsets in boxing history.

Tyson went into the fight the undefeated heavyweight champion and at the time was considered the pound for pound number one fighter in the world. Douglas had a good record too at 29-4-1, but the odds on him winning were still 42-1.

Douglas dominated most of the early rounds, with Tyson looking slower than usual and unfocused. In the eighth round, Tyson managed to knock Douglas down and he was nearly counted out. However, in the final round, Douglas landed a solid uppercut that knocked Tyson down for the first time in his career.

Buster Douglas Mike Tyson

Don King Productions

Muhammad Ali vs Sonny Liston (1964)

This fight is another contender for the biggest upset in boxing history. Going into the fight, Sonny Liston was World Heavyweight Champion. He had won the title after beating Floyd Patterson in a first-round knockout that demonstrated his dominance.

Muhammad Ali was a younger fighter but had already made a major impression. He spent the weeks leading up to the match riling Liston up, hoping that he would be too angry with the sassy young fighter to fight his best.

That’s exactly what happened. After six punishing rounds, Liston spat out his mouthguard and admitted defeat. His shoulder had essentially been paralyzed and there was no point continuing. In that moment, Ali began his first reign as the World Heavyweight Champion.

The 1965 rematch between Ali and Liston also ended in a win for Ali, though this match was so one-sided and over so quickly that many suspected that it was a fixed fight. Liston’s suspicious death only a few years later adds support to this theory as it is likely he was murdered.

Hasim Rahman vs Lennox Lewis (2001)

Lennox Lewis’ 2001 title defense bout against Hasim Rahman took place in Brakpan, South Africa and was billed as “Thunder in Africa”. Everyone expected Lewis to bring most of the thunder — this would be his fourth title defense and he was gearing up to fight Mike Tyson later that year.

Lewis should have taken the fight, and his opponent, a bit more seriously. He didn’t train at altitude, despite the fact that Brakpan is 5000ft above sea level, and only arrived in South Africa a few days before the fight. Hasim Rahman, on the other hand, had given himself nearly a month in South Africa to adjust. 

Despite this, the first four rounds were close, with each fighter holding their own, though by the end of the fourth round, Rahman was dominant. Lennox tried to land a knockout blow during the fifth round, but as it came to a close, it was Rahman who successfully knocked out the champion and won the title. 

It was a short-lived time as champion. In November that same year, Rahman faced Lennox again in a rematch. Lennox won with a fourth round knockout and reclaimed his titles. Sometimes, the underdog’s time on top is very brief. 

Corrie Sanders vs Wladimir Klitschko (2003)

When Wladimir “Dr Steelhammer” Klitschko and Corrie “The Sniper” Sanders met in a match billed as “The Next Big Thing”, Klitschko was the reigning WBO heavyweight champion and Sanders was rated 11th

However, no matter how much of an underdog he might be, a southpaw always has a decent chance of upsetting an orthodox boxer. That’s just what happened here. Sanders hadn’t spent much time in the ring since a 2001 loss to Rahman but still managed to knock Klitschko down in the second round.

Muhammad Ali vs George Foreman (1974)

Even people who don’t follow boxing have heard of the Rumble in the Jungle, a fight so famous its name has entered pop culture. This showdown between reigning WBA and WBC heavyweight champion George Foreman and Muhammad Ali was meant to showcase Foreman’s talents.

Instead, it became the first fight where Ali demonstrated his rope-a-dope technique of allowing his opponent to tire himself out early in the fight so that Ali could easily step in with a knockout blow and end it.

Foreman was the younger man and a fierce fighter, but Ali had experience on his side. After several rounds of Ali letting Foreman tire himself out, Ali attacked in earnest during the eighth round. He knocked Foreman down with a 5-punch combination and that was the end of one of the greatest upsets in boxing.