Biggest UFC Middleweight Title Upsets Ever as Sean Strickland Shocks the World... Again
A pair of boxing gloves - Source: Unsplash
Sean Strickland shocked the world at UFC 328 on May 9th at the Prudential Center in Newark when he outpointed the feared and formerly unbeaten Khamzat Chimaev to become a two-time middleweight champion of the world. After a build-up fuelled by plenty of bad blood, very few gave the brash American any chance of surviving the monstrous Chechen, let alone actually defeating him. However, after withstanding a first-round wrestling onslaught, the newly minted champion managed to turn the tide.
Underdog Strickland Stuns Chimaev
Heading into the clash, online betting sites gave the challenger very little hope of regaining the title that he lost to Dricus Du Plessis in January 2024. The popular Lucky Rebel sportsbook listed Strickland as a +385 underdog, with the defending champion installed as a whopping -500 favorite. However, Chimaev was already gassed by the start of the second round, with a brutal weight cut of a reported 45 pounds clearly taking its toll. Strickland would take advantage, dominating both on the ground and on the feet to win the round, before peppering away with the jab to narrowly edge the third as well.
Chimaev would find his second wind in the fourth, repeatedly pushing Strickland back with strikes and relentless pressure to level things up at 2-2, meaning that the winner of the fifth round would likely emerge as champion. The Chechen behemoth managed two takedowns in the fifth but inflicted very little damage once he had his opponent down, and Strickland would quickly get back to his feet and fire off that ram-rod left jab again. Two of the judges determined that he'd done enough, handing the American a razor-thin split decision victory, ending Chimaev's unbeaten streak.
15 minutes away from #UFC328 💪
— Lucky Rebel (@LuckyRebel__) May 10, 2026
It's all eyes on Chimaev (-500) vs. Strickland (+385) in the main event
The undercard underdogs:
Diaz (+700)
Stephens (+335)
Brady (+185)
Cortes-Acosta (+116)
Van (+135)
Whose corner are you in tonight?
More lines: https://t.co/6FfIF6JlWG pic.twitter.com/bPDy6K9rEd
The 185-pound division has provided no shortage of shocking upsets. In fact, no division in the UFC has offered up as many shockers as the middleweight division. But what are the biggest upsets of all time? Let's take a look.
Chris Weidman Knocks Out Anderson Silva
Heading into July 2013's UFC 162, middleweight champion Anderson Silva was considered somewhat unbeatable. The Spider had ruled over the 195-pound division for almost seven years, and he had done so with an iron fist. The Brazilian had made ten defenses of his title, still the most of all time, beating names such as Dan Henderson, Vitor Belfort, and eternal rival Chael Sonnen twice.
Number one contender Chris Weidman wasn't expected to put up much of a fight against Silva, despite his unbeaten 8-0 record. But it was exactly that underdog status that ultimately propelled him to victory. The Spider, clearly feeling far superior, started his usual showboating in the second round, and ultimately, it would be his demise.
While the Brazilian was mocking Weidman's strikes, exaggeratedly feinting one way then the other, the "All-American" would catch the long-reigning champion with a looping right hook, shockingly dropping Silva to the deck. Weidman would then pile in with vicious ground and pound, knocking out Silva and securing arguably the biggest upset win of all time. He would then beat Silva again in an immediate rematch when he brutally broke Silva's leg as he checked one of the Spider's attempted calf kicks. The two triumphs remain two of the UFC's most iconic moments.
Michael Bisping Stuns Luke Rockhold on Short Notice
Luke Rockhold would ultimately dethrone Weidman two-and-a-half years on from the All-American's stunning title upset, and he was supposed to go on a long reign as champion. The classy striker racked up his fifth straight stoppage win when he claimed the title, and an immediate rematch against Weidman was supposed to mark the first successful defense of the gold. Then, when Weidman pulled out of the fight due to an injury, Rockhold was made an even bigger favorite to beat the late replacement, Michael Bisping.
The British veteran accepted his maiden title challenge on just 17 days' notice at UFC 199, and considering the fact that Rockhold had already beaten him by submission less than two years earlier, Bisping was given little to no hope of upsetting the champion. Ultimately, however, no one told him that.
Less than four minutes into the first round, Bisping landed a brutal left hook onto the wide-open chin of Rockhold, shockingly dropping the champion. Rockhold would get back to his feet only to get drilled with the exact same punch, falling to the ground again. The challenger would then pile in three more vicious shots to the downed champion to secure the knockout win and claim the title at the age of 37.
Sean Strickland Dominates Israel Adesanya
Israel Adesanya was, and perhaps still is, considered by many to be the second-best middleweight ever behind Anderson Silva. The Last Style Bender racked up five successful defenses of the middleweight title before being knocked out by rival Alex Pereira at UFC 281. Adesanya would then reclaim the title by returning the favor, knocking out Pereira and beating the fearsome Brazilian for the first time in their epic three-fight trilogy - the first of which came in the pair's kickboxing days.
The first defense of Adesanya's second title reign came against the brash Strickland, whose verbal onslaught in the build-up to the fight was relentless. Many thought that the champion would punish the American for his words on fight night in Sydney, Australia, but Strickland would go on to prove that he wasn't all talk.
Strickland would shockingly drop the confident champion in the opening round, clearly knocking Adesanya off his game. From there, he would go on to dominate the fight, relentlessly pressing forward and taking the fight to the Nigerian-born New Zealander. In the end, Strickland secured a wide unanimous decision victory, shocking the world as a 3/1 underdog.
