Top 5 Biggest UFC Upsets of 2023 and One to Target in 2024

Massive underdog victories and inexplicable upsets were the name of the UFC game in 2023. We break down the best ones and bring you one that could be coming in 2024 in our full recap below.

Rohit Ponnaiya - Betting Analyst at Covers.com
Rohit Ponnaiya • Betting Analyst
Dec 24, 2023 • 18:00 ET • 4 min read
Sean Strickland UFC
Photo By - USA TODAY Sports

2023 was a banger year in the UFC with some incredible fights, highlight-reel finishes, and shocking upsets.

Anyone who digs into the UFC odds knows that there's nothing more tantalizing than backing a fighter at big plus money in a sport where anything can happen. And those who like to bet on underdogs were rewarded with some big money this year, especially in several headline events. 

With the final bell about to sound for 2023, here are the five biggest UFC betting upsets of the year and one possible upset to target early in 2024. 

Top 5 Biggest UFC Upsets of 2023

No. 5: Nicolas Dalby (+455) vs Gabriel Binfim (-625)

Why the odds were so lopsided: When I came up with this list I didn't necessarily choose the biggest plus money underdog winners because I wanted to emphasize the bigger fights over upsets on the prelims.

That's partially why I chose Dalby over Elves Brener who had not one but two victories as a +500 underdog, beating Zubaira Tukhugov by decision in February before pulling off another shocking upset in a war against Guram Kutateladze five months later. 

While Brener is a 26-year-old prospect who was a bit of an unknown commodity to UFC oddsmakers, Dalby had just turned 39 and was viewed as a stepping stone for Bonfim. 

The 26-year-old Bonfim was one of the fastest-rising stars in the promotion and had gone a perfect 15-0 in his career. He had steamrolled his first three opponents in the octagon, submitting Trey Waters, Mounir Lazzes, and Trevin Giles in the first round and the aging Dalby was expected to be the next notch on his belt.

Instead, Dalby poured on the pressure in the second round against Bonfim and managed to overwhelm him with strikes. 

Why we should have seen this upset coming: Any time a young fighter moves up the rankings, there are times along the way where they see a significant bump in competition. Bonfim had quickly finished a few mediocre fighters before taking on Dalby who had never been stopped inside the distance in his 30-fight career.

Despite never being a Top-15 welterweight in the UFC, Dalby is a well-rounded, durable, and experienced fighter. He had also gone 4-1 in his previous five fights with three of those victories coming as an underdog. Dalby was the ideal fighter to fraud-check Bonfim and that's exactly what he did by derailing the young Brazilian's hype train.  

No. 4: Dricus du Plessis (+300) vs Robert Whittaker (-400)

Why the odds were so lopsided: Whittaker was widely regarded (along with Max Holloway) as the best fighter in the UFC without a belt. He had gone an impressive 13-2 in his previous 15 trips to the octagon with his only defeats during that span coming against the (now former) middleweight champion Israel Adesanya.

Whittaker is a fighter seemingly still in his physical prime and has few flaws to exploit. He was viewed as being too well-refined and technical for the raw du Plessis to defeat.

However, Whittaker's typical jab-cross-headkick combo proved predictable for DDP who figured out the timing of his strikes. Du Plessis dropped Whittaker in the second round and then swarmed a retreating Whittaker to put him away with a barrage of unanswered punches.

Why we should have seen this upset coming: While Whittaker had established himself as an elite middleweight with a well-rounded skillset, he had also shown a worrying tendency to stand and bang with dangerous strikers.

Du Plessis was a rising contender who had gone 5-0 in the UFC and had an incredible 95% finish rate across 19 career MMA victories. The 29-year-old South African is also a physical specimen with explosive athleticism and power.

Although du Plessis had been criticized in the past for gassing out after the opening round, he had recently undergone surgery to fix a breathing issue he had been having for years. He proved that his cardio had leveled up by aggressively hunting down Whittaker for the finish in the second round.

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No. 3: Bobby Green (+400) vs Grant Dawson (-550)

Why the odds were so lopsided: Dawson was a young up-and-comer who had recently cracked the rankings and had compiled a 9-0-1 record in the octagon. His relentless chain-wrestling and high-end grappling were perceived as being too much for the 37-year-old Green who had gone just 3-4 in his last seven fights. 

While Green has enjoyed a long and successful tenure in the UFC, he was never quite good enough to be anything more than a gatekeeper for the Top 15 in the lightweight division. That's because while he's well-rounded, he doesn't stand out in any area.

When their headline event took place in October, Green didn't waste any time. He dropped Dawson with a straight left and then finished him with hammerfists just 33 seconds into the opening round. 

Why we should have seen this upset coming: While Dawson had strung together a highly impressive winning streak, he hadn't beaten a single ranked fighter along the way. He was also heavily reliant on his grappling and didn't look comfortable on his feet or react well to eating shots when he almost lost to the mediocre Ricky Glenn two years ago.

However, while Green had a clear path to victory with his solid takedown defense and high-volume striking, few could have predicted him winning the way he did. Green had picked up just one other win by KO/TKO since 2013 — a span of 22 fights. 

No. 2: Alexa Grasso (+500) vs Valentina Shevchenko (-675)

Why the odds were so lopsided: Shevchenko was the unquestioned GOAT of the women's flyweight division after seven successful title defenses at 125 pounds. Her only defeats in the UFC had come in competitive tilts against the all-time GOAT Amanda Nunes at bantamweight and she had typically dominated her challengers at flyweight.

Shevchenko had virtually cleaned out her division and Grasso was seen as the next casualty. Grasso entered this bout on a four-fight winning streak but had gone just 3-3 in her previous six bouts. Her lack of ground game was seen as a hole that Shevchenko could exploit and her low finish rate (just one of her previous nine wins had come by stoppage) made it extremely unlikely that she could pull off the upset. 

But that's exactly what Grasso did, winning the boxing exchanges and fighting off Shevchenko's grappling on the mat before taking her back standing up and submitting her in the fourth round. 

Why we should have seen this upset coming: As dominant as Shevchenko had been for most of her title run, she was coming off a decision win over Talia Santos where she needed to rally late to turn the tide. While she took a close split decision there, she looked more vulnerable than ever and it was fair to question if she was starting to slip. 

Meanwhile, while Grasso had lost three fights earlier in her UFC career those had all come at strawweight and she had gone a perfect 4-0 since moving up to her more natural weight class. With her crisp boxing, pressure, and durability, she clearly had a path to victory against Shevchenko if she could outwork her on the feet.

What was even more surprising than Grasso winning outright was her managing to submit a superior grappler. Backing Grasso to win by submission would have paid out at +1,600. 

No. 1: Sean Strickland (+540) vs Israel Adesanya (-770)

Why the odds were so lopsided: Strickland opened at +350 with Adesanya at -430 but money poured in on the reigning champ and his line moved as high as -770 before closing at FanDuel.

Adesanya was making a case as the greatest middleweight in MMA history with just one career loss at 185 pounds and eight title wins. A highly-skilled kickboxer with blinding speed and flawless technique, Adesanya could pick apart fighters at range or starch more aggressive foes with counterstriking in the pocket. 

The only middleweight that Adesanya had ever lost to was another elite kickboxer (and newly-crowned light heavyweight champion) in Alex Pereira. Adesanya avenged that defeat with a KO win against Pereira just five months before this bout and Strickland had been knocked out in the first round by Pereira just a year before. 

Strickland's popularity due to his outspoken personality and Adesanya having already cleaned out the rest of the contenders (with du Plessis injured at the time) were seen as reasons why he got this title shot with many questioning if he truly deserved it. He proved he did by almost finishing Adesanya in the first round and outstriking him 137-94 en route to a unanimous decision victory.

Why we should have seen this upset coming: This is one of the few fights that — even in hindsight — would have been almost impossible to predict.

While there were questions about how Adesanya would perform against an elite grappler and we knew that he could be caught by a devastating heavy-hitter like Pereira, getting outpointed in a five-round striking exchange with a meat-and-potatoes boxer like Strickland seemed impossible.

That said, this was a situational spot to avoid. Coming off an emotional knockout victory against Pereira and looking ahead to a battle to be "Africa's champion" against du Plessis, this was both a letdown spot and a look-ahead spot for Adesanya who didn't seem to take Strickland seriously. At least not until Strickland almost finished him with a flurry of punches in the opening round. 

Following that defeat, the 34-year-old Adesanya announced he'd be taking a break from the sport and might not return until 2027 — another indication that he was mentally and physically fatigued.  

One UFC upset bet to target in 2024

Ilia Topuria (+148 at FanDuel) vs Alexander Volkanovski (-192)

Looking at the early UFC betting odds for 2024, several lines look a bit too wide (especially on the women's side where Amanda Lemos is +285 against Tatiana Suarez), and this line is relatively close. However, Volkanovski losing his featherweight belt would still count as a major upset in the MMA world and I expect this line to be even wider by the time UFC 298 rolls around.

Volkanovski has been a dominant champ with five consecutive title defenses at 145 pounds. He's separated himself from No. 1 contender Max Holloway and was a massive favorite against two of his last three title challengers (-400 vs. Yair Rodridguez and -770 against the Korean Zombie) and came through with lopsided victories. 

That said, Volk is coming off a brutal head-kick knockout from Islam Makhachev when he cut weight on short notice for a lightweight title fight in October. Four months might not be enough time to recover from a knockout like that, especially against a dynamic striker like Topuria who has won by KO in three of his last five fights. 

It's also worth mentioning that Volkanovski is now 35 years old, which is right around the age when many fighters in the lower weight classes begin a steep decline against top competition.

It seems wild that Volk could lose his belt less than a year after being considered the best pound-for-pound fighter in the UFC, but we've seen greats like Adesanya, Nunes, Shevchenko, and Kamaru Usman all knocked from their perch over the last few years and Alexander the Great could be next.

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Betting Analyst

With a background playing soccer, rugby, and boxing, combined with a journalism degree, it's little surprise that Rohit gravitated towards the world of sports betting. He specializes in betting on UFC and college basketball, two sports where the eyeball test can tell you a lot more about matchups than any analytics. Rohit has years of experience handicapping NFL and NBA games as well as niche betting markets such as politics and Oscar odds. He's also the resident CFL expert and formerly hosted "The Chez and Ro Show" with former CFL star Davis Sanchez.

You can catch Rohit breaking down every UFC event with Joe Osborne on "P4P Picks" on the Covers YouTube channel and he also has regular appearances on "Before You Bet" with Joe. In addition, he's a regular guest on "By The Book" on the Monumental Sports Network and makes guest appearances on VSIN's "The Handle" and CBS Sports.

Rohit primarily makes his bets at bet365, which offers a wide variety of prop markets, but also has accounts at several others so he can shop around for the best prices. For Rohit, bankroll management is key. He believes you should never bet what you can't afford to lose and maximize those few betting opportunities where books misprice a line.

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