Top 10 Upsets In Boxing And UFC History

Conor McGregor is hoping to cause one of the greatest upsets in the history of combat sports when he takes on Floyd Mayweather in Las Vegas on August 26. Few are giving him a hope against the 49-0 boxer, but there are plenty of examples from history of men triumphing against the odds in the ring or in the octagon. Here are the 10 greatest upsets in the history of boxing and UFC.

10. Tyson Fury v Wladimir Klitschko – November 28, 2015

The champion had not been beaten, or scarcely even troubled, for over 10 years, but that didn't faze Tyson Fury as he headed to Germany on a mission to dethrone Wladimir Klitschko. The Englishman was available at around 7/2 to win this one, despite his flawless 24-0 record. Klitschko’s discipline and power looked certain to be enough against the unorthodox giant who had been put down in the past against much lesser names. What transpired was a baffling display from Fury which confused the champ into barely throwing a right hand throughout the fight. Fury took home a unanimous decision from Germany – the least likely outcome of the evening, according to the bookmakers. The only downside is, we haven’t been able to see it again.

9. Joey Beltran v Rolles Gracie – February 6,2010

It was thought that Rolles Gracie was going to be the next great name of the famous Brazilian family, so much so that he was priced at 1/15 on his UFC debut against Joey Beltran who had an MMA record of 10-3. Much was expected of Gracie but he delivered absolutely none of it, tiring fast and being knocked out in the second round by a man whose record now stands at 17-14. Gracie’s UFC contract was immediately terminated and he has not returned to the company. Anyone who as backing Beltran at 15/2 would have been very happy indeed.

8. T.J. Dillashaw v Renan Barao – May 24 2014

Then UFC lightweight champion Renan Barao had won 31 fights on the spin since losing his professional debut. He was winning fights with a wide array of techniques and was rated in the pound-for-pound top three by 2014. Up stepped T.J. Dillashaw who, looked a meagre challenge with a record of 9-2, especially as he had lost two fights before to Raphael Assuncao. Dillashaw was a big underdog at 7/1 but he didn’t look like one as he dominated the contest for five rounds, knocking out the champ in the final stanza. He would knock Barao out in four when they rematched the following year.

7. James Bradock v Max Baer – June 13 1935

So shocking was this result, the film Cinderella Man was made about James Bradock’s achievement. Braddock was a journeyman heavyweight who had a record of 49-25-7 when he got his first shot at the world title. Injuries had cost him throughout his career and it had looked like his time in the ring had finished. However, his string of seven fights without defeat from 1933-35 got him a surprise shot at the gold. Max Baer had only just won that gold, but having knocked out Max Schmeling and Primo Carnera in his last two bouts, he was one of the most feared men on the planet. More powerful, with a huge reach advantage, Baer was expected to sweep Braddock aside, but the New Yorker had a different idea. Braddock ground out a points win over 15 rounds to capture the world title and shock the world.

6. Frankie Edgar v BJ Penn – April 10, 2010

The records really don’t tell the story in this one as Frankie Edgar (12-1) was a huge underdog when he face BJ Penn (15-5-1) for the UFC lightweight title in 2010. Bookies were offering 7/1 on The Answer, despite his impressive record, and some people cashed in. It was close but Edgar deservedly won a tight decision over the two-weight world champion, then proved his superiority by winning the rematch as well. Penn was one of the superstars of the sport at the time but, whilst still a legend of the game, has now been relegated to an also-ran. Still fighting but with five straight losses, the upset defeats to Edgar really cost him.

5. Antonio Tarver v Roy Jones Jr II – May 15 2004

Roy Jones was the greatest fighter on the planet back in 2004, the pound-for-pound king with a record of 49-1 and his only defeat coming via disqualification. He had just stepped up to heavyweight and won a world title, having become a world champion at middleweight, super middleweight and light heavyweight. He had also most recently returned to 175lbs and beaten Antonio Tarver to remain the man at light heavy. Jones had not looked great in that first clash with Tarver, but nonetheless he was the runaway favourite to beat him when they organised the rematch for six months later. The Magic Man shocked the world with a second round stoppage and sent Jones’ career spiralling downhill from there, never to win a world title again.

4. Holly Holm v Ronda Rousey – November 15 2015

Ronda Rousey was the biggest name in the UFC in November 2015 – this was a month before Conor McGregor knocked out Jose Aldo to overtake her – and her unbeaten run in MMA looked set to continue against Holly Holm. Rousey’s record was 12-0 across four promotions and only one of her 12 wins had gone past the first round as she routinely submitted opponents with her armbar. Holm was also undefeated (10-0) and a former world champion boxer so she was clearly a threat, but Rousey had so easily despatched all previous foes, it didn’t seem at all likely Holm would fair any different. However, The Preacher’s Daughter dominated round one then landed a perfect head kick in the second to knock out Ronda and send her spiralling into, what looks certain to be retirement.

3. Randy Turpin v Sugar Ray Robinson – July 10 1951

Arguably the greatest fighter in history, Sugar Ray Robinson came to England as part of a European tour which saw him fight in six countries in just two months in 1951. Perhaps this was a poor idea but he still turned up at Earls Court Arena with a record of 128-1-2, so he was not expected to struggle with British hope Randy Turpin. Whilst Turpin was very decent, with a record of 40-2-1, no one was thought to be on Robinson’s level, never mind Turpin who had lost to people nowhere near Sugar Ray’s level in the past. It wasn’t a lucky punch or a dodgy disqualification, it was 15 rounds of pugilism over which Turpin beat Robinson, taking the decision and the world middleweight title in the process. Robinson knocked out Turpin in the New York rematch later that year, but the shock in London cemented Turpin’s place in history.

2. Matt Serra v Georges St-Pierre – April 7 2007

Georges St-Pierre may have only won the UFC welterweight championship in his previous bout but he was considered one of the pound-for-pound very best in the sport. Matt Serra had just won The Ultimate Fighter but had a record of just 9-4 and had been beaten by some average fighters. Perhaps St-Pierre wasn’t taking Serra all that seriously, the bookies were offering 11-1 on the New Yorker, and if that was the case then it cost him dearly. It took just over three minutes of the first round for Serra to knock out GSP and claim the welterweight title – causing one of the greatest upsets in the history of combat sports.

1. Buster Douglas v Mike Tyson – February 11 1990

At the start of the 1990s, Mike Tyson was one of the most dominant champions in boxing history. Iron Mike’s record stood at 37-0, and he knocked 33 of those opponents out. Buster Douglas was a solid enough fighter, he had beaten Trevor Berbick and Oliver McCall to earn this title shot. However, he had lost four times, being knocked out on three of those occasions. Douglas was as long as 42/1 to capture the heavyweight title and no one was taking even that giant price. Fortunately for the underdog, Tyson had not been training or taking the fight seriously at all and it showed. Douglas had the better of the fight before knocking out the champ in the 10th round and causing the greatest upset in combat sport history.