Biggest Betting Upsets In UFC History

Second-Round TKO—UFC Vegas 7, Aug. 22, 2020

No prospect should ever be as large of a favorite as Mariya Agapova was going into her fight with Shana Dobson.

Agapova had all the advantages on her side, as she’d finished nearly all of her nine victories up to that point. Incredibly aggressive with her striking approach, the “Demonslayer” became known for battering opponents before submitting them on the ground. Against Dobson, she was on her way to another notch in her belt.

Unfortunately for Agapova, Dobson was tougher than the prior bunch and survived the opening onslaught. A visibly gassed Agapova found herself on the receiving end of a second-round beating, and that was that.

Dobson’s victory may have been a fluke, but it was one that some lucky bettors will forever be grateful for.

Second-Round KO—UFC 193, Nov. 11, 2015

Among any upset in MMA history, Holly Holm vs. Ronda Rousey is probably the silliest in hindsight.

Holm was stylistically always a nightmare for Rousey, and the likelihood of a Rousey victory was never a sure thing. However, the dominance Rousey displayed during her previous 12 fights was enough to keep many believing that she’d breeze through Holm, a relative newcomer.

Instead, it was about as masterful a performance as Holm could have imagined. To cap it off, “The Preacher’s Daughter” scored the mother of all knockouts, head-kicking Rousey to become just the second bantamweight champion. While it shouldn’t have been an upset in retrospect, it will forever be a crazy and impactful moment.

First-Round TKO—UFC 69, Apr. 4, 2007

No. 3 and 4 on this list start approaching aberration territory if the rematches are anything to go by.

Matt Serra was a talented fighter at his best, but essentially a UFC reject after getting a spot on Season 4 of The Ultimate Fighter. By winning, Serra earned a title shot against the new superstar phenom champion Georges St-Pierre.

As one of the more underrated grapplers in MMA history, Serra’s upset of “GSP” was just one of his two career victories from strikes. Despite the numbers placing this one at No. 3, many still consider it the biggest upset ever. After seeing St-Pierre lay waste to Serra in the immediate rematch and then go on to become arguably the greatest UFC fighter in history, it remains a fair claim.

Second-Round Submission—UFC 269, Dec. 11, 2021

No one believed in Julianna Peña as much as she believed in herself ahead of UFC 269, and that was all that mattered.

After a rough first round that saw Amanda Nunes put on a typical thumping, Peña let loose in the second round to shock the world. Starting to chip with her jab, Peña upped her engagement and drew Nunes into an uncharacteristic firefight as the dual-division champion grew tired.

Peña found her way to Nunes’ back after trading blows, locked in a rear-naked choke without hooks and got the tap over the greatest female fighter of all time. The loss snapped Nunes’ dominant 12-fight win streak, but like with Serra, it was one-way traffic for Nunes in the rematch.

First-Round DQ—UFC Vegas 52, Apr. 23, 2022

Once again, prospects should never be favored this much. However, this is by far the weirdest situation out of all fights on this list.

After being publicly slammed by UFC President Dana White following his Phil “CM Punk” Brooks victory in June 2018, Mike Jackson surprisingly got another fight in the promotion four years later. He welcomed another legitimate prospect to the octagon, similar to how he did with Mickey Gall in his debut, and his eyes paid the price for it.

Barry was disqualified for eye-gouging and consequently released from the promotion. It’s one of the more bizarre UFC fights one could ever see.

The following five upsets aren’t in order of largest differences like the previous ones, but they’re still among the most significant ever. In terms of their immediate impact and the long-term ripple effects, they shifted numerous future moneylines and created (and shattered) multiple fighters’ careers along the way.

Fifth-Round TKO—UFC 173, Mar. 24, 2014

The moment T.J. Dillashaw landed a single punch, Renan Barao’s phenomenal career immediately began to unravel.

Originally supposed to be Raphael Assuncao, Dillashaw filled in to save the day and became a star, outclassing a fighter many considered the pound-for-pound best at the time. Dillashaw’s trouncing of Barao was the end of one legacy and the start of another.

Unanimous Decision—UFC 112, Apr. 10, 2010

Frankie Edgar’s first win over B.J. Penn was similar to a changing of the guard like Dillashaw vs. Barao. However, the consensus was that Penn was robbed of the victory.

“The Prodigy” was undeniably in peak form heading into the Edgar bout, and it had all the makings of being a vintage Penn performance. It was still a solid effort, but closer than he would have liked, and he lost his title as a result. The same couldn’t be said for their rematch and definitely not the unnecessary trilogy years later.

Ultimately, this fight likely made many bettors angrier than most, as they didn’t get their money back in part two.

First-Round KO—UFC 217, Nov. 4, 2017

There was just something in the air at UFC 217. All three champions lost their titles that night, starting with the most dominant of the trio, Joanna Jędrzejczyk.

Like Rousey in her prime, Jędrzejczyk was on a reign of terror that practically began as soon as the strawweight division did. A Muay Thai ace, Jędrzejczyk’s striking was unmatched at 115 pounds. Against her, Rose Namajunas’ best chance presumably was on the ground with her grappling threats.

Instead, “Thug” entered a flow state and styled on Jędrzejczyk briefly before putting her away with punches just over the three-minute mark. Namajunas went on to become the first two-time female UFC champion.

First-Round KO—UFC 199, June 4, 2016

Stories don’t get much better than Michael Bisping’s rise to the top of the mountain.

Bisping’s two-week notice upset knockout of Luke Rockhold was such a wild and memorable victory that many fans completely forget—or didn’t know in the first place—that the fight was a rematch. Two years prior, Bisping succumbed to a second-round one-armed guillotine submission against Rockhold in Sydney, Australia. The American Kickboxing Academy (AKA) staple had only improved since, achieving champion status by dethroning Chris Weidman.

In the rematch, “The Count” needed the assistance of old “Left Hook Larry” to send Rockhold spiraling for an epic victory.

First-Round KO—UFC 70, Apr. 21, 2007

When Mirko “Cro Cop” Filipovic entered the UFC after PRIDE FC was bought out, fans assumed it was only a matter of time before the icon was fighting for gold. Well, that all got halted by Gabriel Gonzaga.

Cro Cop’s signature moves were his head kicks. “Right leg hospital, left leg cemetery,” the Croatian was famously quoted saying. However, on that night against the relatively untested Brazilian, he had the tables entirely turned on him.

The fight was as close as Cro Cop ever got to tasting UFC gold as Gonzaga’s violent head kick finish led him to a title fight against Randy Couture.