Spend your life betting mega longshots on UFC and you will likely face a lifetime of losses. There are reasons why the oddsmakers set a contender as being super long to win.

Biggest Upsets In UFC History

  • Mike Jackson vs. Dean Barry, April 23, 2022; UFC Vegas 52

  • Julianna Pena vs. Amanda Nunes, December 11, 2021; UFC 269

  • Matt Serra vs. George St.-Pierre, April 7, 2007; UFC 69

  • Holly Holm vs. Ronda Rousey, November 14, 2015; UFC 193

  • Shana Dobson vs. Maiya Agapova, August 22, 2020; UFC Vegas 7

Sometimes, though, gamblers outsmart the folks who make the lines. Or else they just get lucky.

Either way, there is nothing like the rush of turning small money into big money when a grappler comes through with a surprise move that gets punters on their feet and bookmakers digging into their pockets.

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Here are five matches that ended with big surprises that benefited bettors and put bookies on edge. 

Mike Jackson vs Dean Barry

Maybe a disqualification of Dean Barry was the likeliest way for Mike Jackson to win this match with a moneyline that had him at +700 in UFC odds. Barry’s dirty deed took place during the first round when the match seemed to be going as predicted.

Barry snagged a knockdown and Jackson got to his feet, attempting to short-circuit the action, clinch his opponent and get through the round. But Barry responded strongly.

He tried pushing Jackson away, via his face, and wound-up gouging Jackson’s eye, which led to the ringside doctor shutting down the match. Barry was disqualified and Jackson emerged as a victor with a medical issue. 

The payoff: A $100 wager earned $700. 

Julianna Pena vs Amanda Nunes

Lady luck smiled upon bettors during the second round, when Julianna Pena put the choke on Amanda Nunes to generate a +650 windfall for canny gamblers.

The first round landed well in the favour of the favourite. But Pena was on fire from the start of the second and she won the old-fashioned way, going punch for punch against her more seasoned opponent, landing harder shots and finally taking her down.

Nunes’ tap-out came 3:26 into the second round.

The payoff: A $100 wager earned $650.

Matt Serra vs George St.-Pierre

Dubbed the “greatest upset in UFC history”, this showdown had Matt Serra set up at whopping +850 if he were to defeat the seemingly unstoppable George St.-Pierre. You really had to believe in Serra if you were willing to bet on him...

But the underdog clearly believed in himself and he did what seemed like the unthinkable: he landed a crunching blow behind St-Pierre’s ear, followed with a barrage of punches and forced St.-Pierre to have the ref cease the fight at 3:25 into the first round.

Serra celebrated his surprise win with a cartwheel in the octagon. No doubt, some lucky gamblers did the same thing at home.

The payoff: A $100 wager earned $850.

Holly Holm vs Ronda Rousey

Reigning as the queen-bee of UFC, Ronda Rousey seemed like a shoo-in to beat her lesser known contender, Holly Holm, a +900 underdog, in this title fight. But Holly Holm would not be denied.

Holm came out swinging and by the end of the first round, Rousey was already bleeding. Round-two did not go better for the favorite, and she hit the mat, for a final time that night, following a knock-out kick to the head.

With that, Holly Holm took the championship and those who believed in her were rewarded with a hefty payout. According to USA Today, her team won a six-figure sum by betting on their girl.

The payoff: A $100 wager earned $900.

Shana Dobson vs Maiya Agapova

On paper, this should have been a walk in the park for Maiya Agapova, with her 9-2 MMA record, against Shana Dobson, who stood at 4-4 in MMA outings. Clearly, the oddsmakers agreed: They had Dobson as a +950 underdog who began at +500.

The first round was surprisingly even, though all hell broke loose in the second. Dobson managed to get a dominant position against her opponent, brutalized her with a storm of punch and won by TKO at 1:38 into round two.

Gamblers with the guts to go for Dobson thrilled to her post fight comment: “We saw this coming. We’re excited but we’re not surprised.”

The payoff: A $100 wager earned $950.


Michael Kaplan is a journalist based in New York City. He has written extensively on gambling for publications such as Wired, Playboy, Cigar Aficionado, New York Post and New York Times.

He is the author of four books including Aces and Kings: Inside Stories and Million-Dollar Strategies from Poker’s Greatest Players. He’s been known to do a bit of gambling when the timing seems right.