Prime Picks: Biggest Betting Upsets in UFC History

By Jay Pettry Mar 30, 2020


Editor’s note: Not all bouts could be accounted for in the data. Whenever possible, these odds came from the same sportsbook to keep the information uniform. Your numbers may vary. With this in mind, Holly Holm closed at +525 prior to her upset knockout of Ronda Rousey at UFC 193.

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The Ultimate Fighting Championship has put on over 5,500 fights over the years, and the lion’s share of them throughout the promotion’s modern history featured betting odds. Although some upsets may be considered more historic when factoring in context or more sizeable when determining the actual amounts of bets placed on fights, these strictly come from the magnitude of the underdog’s betting line.

Johnny Eduardo (+735) def. Eddie Wineland (-935)
UFC Fight Night 40
May 10, 2014 | Cincinnati

The biggest betting upset in UFC history did not come in a title bout or on a pay-per-view card. In fact, it did not even take place on the main card of a UFC Fight Night event. This bantamweight bout between a former World Extreme Cagefighting champion Wineland and a well-traveled Brazilian in Eduardo was on the Fox Sports 2 preliminary portion of a show in Cincinnati.

This was standard UFC Fight Night fare, headlined by a thriller between Matt Brown and Erick Silva. Eight different fighters sprang upsets by the time it was over, but none were more convincing than Eduardo, who returned from a lengthy layoff to lay waste to his opponent. Wineland had bounced back from a championship defeat to Renan Barao in which he was drilled in the face with a spinning back kick. He smashed Yves Jabouin less than four months prior and was looking to make one last trek to the title.

Eduardo, meanwhile, dropped his promotional debut but came back in his next outing to take a spirited decision over Jeff Curran and notch arguably the most significant win of his lengthy career. Six years the American’s elder, he worked over Wineland with leg kicks and avoided the power strikes being lobbed at him. Eduardo then unleashed a concussive right hand that set Duneland Vale Tudo rep on unsteady legs. One huge follow-up right hook square on the jaw was all he needed to momentarily separate Wineland from his senses, drawing blood and forcing the dazed-and-confused Indiana native to ask his corner what had happened. As was customary for that era, UFC matchmaker Joe Silva entered the cage to congratulate the winner, and Eduardo nearly lifted him off the ground in celebration.

With that, Eduardo unceremoniously scored the most significant betting upset from an odds perspective in UFC history. His win over a Top 5 contender earned him a fight with Aljamain Sterling some 19 months later. Unfortunately for the aging Brazilian, he only competed once per year from 2014-18 and lost three times in four appearances after that remarkable victory.

Frankie Saenz (+725) def. Iuri Alcantara (-925)
UFC Fight Night 61
Feb. 22, 2015 | Porto Alegre, Brazil

This bantamweight tilt took place on the Fox Sports 1 prelims at an event that saw a UFC record 10 of 11 underdogs emerge victorious. The only favorite to win was Ivan Jorge, who opened the show by taking a decision from Josh Shockley. Otherwise, all bets were off, figuratively speaking, as sportsbooks were crushed by an unexpected turn of events. Saenz served as the grand marshal in the parade of triumphant underdogs.

Though he was far from an undefeated powerhouse, Alcantara had rattled off three victories in 2014 and returned to form after a defeat to Urijah Faber the year prior. “Marajo” was firmly entrenched as a Top 10 bantamweight and may have been a win or two away from an elusive title shot. Standing in his way was an ex-King of the Cage champ who had captured a one-sided decision in his short-notice company debut against Nolan Ticman. Saenz had been regarded as a pressure fighter who was seen as well-rounded without excelling at any specific phase of the sport. With the fight card taking place in Brazil, it was expected to result in a one-sided affair for Alcantara that got the crowd excited. As long as the Brazilian could keep the fight standing or establish top control and work his submission game, he seemed to have a clear path to victory.

What happened was anything but easy for Alcantara. Saenz took him down repeatedly throughout their 15-minute encounter, worked him over with effective ground-and-pound and neutralized the favorite. By avoiding submission attempts and keeping Alcantara on his back for much of the bout, Saenz grinded down the highly touted Brazilian with his pace and aggression. Unable to find a moment to breathe, Alcantara was trapped on the canvas or against the cage and lost all three rounds on two judges’ scorecards. The massive upset did not send Saenz into the upper echelon of the division immediately. Instead, he had to beat Sirwan Kakai to get there, but he never seemed the same after he dropped consecutive bouts to Wineland, Faber and Augusto Mendes.

T.J. Dillashaw (+710) def. Renan Barao (-910)
UFC 173
May 24, 2014 | Las Vegas

The fate of the UFC bantamweight championship was decided in this pay-per-view main event. It was an unexpected headliner, as Vitor Belfort had withdrawn due to the ban on testosterone replacement therapy and opponent Chris Weidman had followed suit after wrecking his knee. Meanwhile, Barao was set to take on Raphael Assuncao before the latter exited with an injury of his own. Dillashaw accepted the fight on less than two months’ notice and entered the championship battle with Barao with everything to gain.

Barao had looked nothing short of sensational in his run leading to and during his time atop the 135-pound division. After losing his professional debut in April 2005, “The Baron” did not suffer another defeat for nearly nine years—a tear that spanned 32 victories and a no-contest and included seven wins inside the Octagon and two more in the WEC. No one expected Dillashaw to hand him his first loss in nearly a decade. The former Team Alpha Male product was unconcerned with taking on a man who had defeated Faber, Wineland and Michael McDonald in devastating fashion in the preceding few years. Instead of allowing Barao to get into his groove by throwing spinning strikes and finding his distance, Dillashaw used his speed advantage to expose the Brazilian. He cracked Barao with a devastating right hand that sent the champ to the floor early on, and the champion never seemed to recover. Finally, after a prolonged beating, Dillashaw managed to take out Barao with a head kick and follow-up punches about midway through the fifth round.

Perhaps the most substantial betting upset in any UFC title fight, Dillashaw’s statement-making performance clocked in as the latest victory in UFC bantamweight history—a record he still holds. The California native came close to matching it in a subsequent title defense against Joe Soto, again booting his adversary in the head in the fifth frame, six seconds quicker than he did against Barao. To say Barao was never the same again is an understatement, as the former champion went on to lose seven of nine bouts following his first Dillashaw beatdown. Although they squared off again a year later, Dillashaw needed less time to seal the deal and it was no less vicious. In that rematch, Dillashaw shifted from a +710 underdog in their first meeting to a -200 favorite.

Matt Serra (+700) def. Georges St. Pierre (-1000)
UFC 69
April 7, 2007 | Houston

Depending on the betting line observed, this legendary encounter falls somewhere between a monumental upset or the biggest upset of all-time. Some odds saw Serra as an 11-to-1 underdog or more leading up to the fight, but the closing line for a major sportsbook gave him the +700 line. Only four -1000 favorites have ever been defeated in the UFC, and St. Pierre was the first by a wide margin. The next came when Mike Wilkinson took out a -1000 Niklas Backstrom, followed by Khama Worthy’s surprise knockout of -1000 Devonte Smith. Most recently, Roxanne Modafferi halted the momentum of -1000 Maycee Barber, who was undefeated at the time. None of those three results had quite the impact of St. Pierre suffering his lone knockout loss in a matchup described as the biggest upset in UFC history on multiple occasions.

Riding high on a six-fight winning streak that saw him avenge his only other defeat to Matt Hughes, St. Pierre had won just one UFC title bout but looked primed to start a long reign atop the welterweight division. The Canadian had only been a pro for five years—with 13 victories, including 10 stoppages—but his head kick knockout of Hughes seemed to indicate a torch-passing moment. Serra, meanwhile, worked his way through the coach-free comeback season of “The Ultimate Fighter” and learned a great deal from one of the advisors: St. Pierre himself. By edging Chris Lytle to win Season 4, Serra punched his ticket as the next contender for the 170-pound strap, even as the MMA community largely imagined him as a figurative lamb being led to slaughter. This was not at all the case. Serra marched down St. Pierre and slung heavy leather, refusing to allow him to establish any kind of rhythm. Seemingly out of nowhere, a monstrous right hand from “The Terror” buckled the Canadian’s legs, and a few more ferocious punches had a squirrelly St. Pierre falling across the cage. Some contend that Serra made St. Pierre tap to strikes, but whether you believe that version of the story or not, he registered the signature victory of his career and did so in spectacular fashion.

With a title reign that lasted just over a year and expired without a successful defense, Serra still scored the most significant upset in UFC history at that time and one that many still see in the same light. Although Serra went on to lose three of his next four fights before hanging up his gloves, St. Pierre never lost again. “Rush” went on to avenge that historic defeat and established himself as one of the greatest mixed martial artists of all-time. Considering St. Pierre’s future success, Serra’s upset looks even more unlikely as the years go by.

Thiago Santos (+660) def. Ronny Markes (-840)
UFC Fight Night 38
March 23, 2014 | Natal, Brazil

One huge upset stood out among an event jam-packed with wayward favorites. A whopping nine betting upsets took place, and a sub-minute drubbing of a fighter who missed weight badly took the cake. Like several other bouts deserving of attention due to their high numerical odds value, this tilt unfolded on the prelims.

Later plagued as a fighter with great potential in desperate need of focus and discipline, Markes was reeling from a third-round knockout loss to the mercurial Yoel Romero. Coming in a full four pounds heavy, he still closed as the biggest betting favorite on the card by a sizeable amount. At the time, Santos was known as a middleweight who barely got through his season of “The Ultimate Fighter Brazil” and lost his UFC debut by submission. Little was expected from Santos entering the bout, and Markes’ failure on the scales indicated he showed little regard for his fellow Brazilian. Santos used the moment as a major statement, ripping a huge liver kick in the opening minute of the bout, likely to Bas Rutten’s delight somewhere. The body kick crumbled Markes, and his aura as a promising prospect was forever shattered. A few destructive follow-up punches alerted referee Mario Yamasaki that the fight required his intervention. “Marreta” was instantly on the map.

The victory earned him a fight against Uriah Hall a few months later, though Santos lost a decision that cooled some of his momentum. From there, he has had surges of brilliance, decimating opponents before losing a fight unexpectedly. Although it would not have been as significant on the sportsbooks, Santos nearly sprang a major upset in July 2019, when he took Jon Jones to a narrow split decision. While experiencing a few hiccups, Santos’ stock has gone up since he upset Markes six years ago. Meanwhile, Markes has since blown his opportunity to proceed in a Professional Fighters League tournament by missing weight and is slated to compete in Bellator MMA when events resume.

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