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Fight Matrix

Biggest Upsets in Martial Arts in the 21st Century

Posted on July 9, 2026 by A. J. Riot

Combat sports run on the promise that anything can happen once the bell rings or the cage door locks. Most of the time, the favorite wins and everyone goes home unsurprised. But every so often the sport delivers a result nobody saw coming, and when it happens on a big, heavily-publicized card, it becomes the stuff fighters get asked about for years. There have been plenty of shocking results across boxing and MMA this century, but these five stand out because of the size of the stage and the names involved.

Evan Holyfield vs. Jurmain McDonald

Evan Holyfield, son of four-time heavyweight champion Evander Holyfield, walked into his 2022 super welterweight bout unbeaten at 9-0 and was expected to move to 10-0 without much fuss. Sportsbooks agreed. In fact, all the sportsbooks from LiveSportsOdds boxing section saw Young Holy as a huge favorite, some even giving -7500 on the guy against journeyman Jurmain McDonald at +2000. McDonald had other ideas, however.


An electrician by trade, McDonald stepped into the ring with a 6-5 professional record, with everyone expecting him to get beaten up by Holyfield junior. At first, it looked as exactly that was going to happen, but “The Shocker” landed an overhand right in Round 2 that put his opponent to sleep.  

The crowd is SHOCKED! There is power behind that Electrician's punch! #TrillerVerz5 @TrillerFight

Jurmain McDonald (7-5) has pulled the upset Evan Holyfield (9-1) pic.twitter.com/1AvmMeR22O

— TrillerTV (@Triller_TV) May 15, 2022

Biaggio Ali Walsh vs. Ronnie Gibbs

Biaggio Ali Walsh, Muhammad Ali’s grandson and a rising PFL lightweight, arrived at PFL World Tournament 7 in Chicago with an unbeaten pro record and odds of -1430 against Ronnie Gibbs at +700. Walsh dropped Gibbs early and looked every bit the heavy favorite. Then Gibbs, fighting in his hometown in just his second pro bout, reversed the momentum in round two and locked in an arm-triangle choke to hand Walsh the first loss of his MMA career in front of a stunned Wintrust Arena crowd.

Nico Ali Walsh vs. Sona Akale

Another of Ali’s grandsons found himself on the wrong side of an upset inside the boxing ring. Nico Ali Walsh, boxing’s version of the Ali legacy, was unbeaten and heavily favored at around -1400 to Sona Akale’s +700 when the two met in Tulsa. Akale, a part-time hip hop artist better known to fans as “Slink Proper,” pressured Walsh for six rounds and walked away with a majority decision that ended Walsh’s undefeated run.

Abubakar Nurmagomedov vs. Pavel Kusch

Abubakar Nurmagomedov is best known to casual fans as part of Khabib Nurmagomedov’s team, the group that clashed with Conor McGregor’s corner after UFC 229, with Abubakar himself getting caught up in the brawl and struck by The Notorious. Back in 2018, he was a rising PFL welterweight who went off at -1420 against Pavel Kusch’s +820 in the PFL’s regular season. Kusch had other plans, catching Nurmagomedov with a rear-naked choke in round two for one of the promotion’s most talked-about early upsets. It’s a reminder of how PFL has grown into a genuine talent destination.

Matt Serra vs. Georges St-Pierre

No list of combat sports shockers is complete without this one. Matt Serra was a massive underdog heading into UFC 69 in 2007, given little chance against welterweight champion Georges St-Pierre. Serra landed a right hand in the opening minute, followed up on the ground, and finished St-Pierre in under two rounds to become one of the biggest title upsets in UFC history.

Holly Holm vs. Ronda Rousey

Ronda Rousey walked into UFC 193 in 2015 as arguably the biggest star the UFC had ever produced, unbeaten and finishing almost every opponent in a round or less. Holly Holm, a former boxing champion making just her third UFC appearance, was written off by most. Holm’s footwork and distance control set up a head kick in round two that knocked Rousey out cold, instantly becoming one of the most replayed moments in MMA history and ending Rousey’s aura of invincibility overnight.

Boxing and MMA will always throw up shocks nobody predicts, but these five happened under the brightest lights, against the biggest names, and that’s exactly why they’re still being talked about.

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