5 UFC headliners that were mismatches on paper

This weekend sees the UFC visit Singapore, and the headline bout has already become one of the more questionable of 2023.

The UFC usually puts together highly competitive headline bouts, but this weekend’s clash between Max Holloway and Chan Sung Jung doesn’t quite fit that bill.

Over the years, we’ve seen a handful of these kinds of headliners that looked like mismatches on paper. Each time they left the fans confused, even if the results weren’t always what people expected.

Here are five UFC headliners that appeared to be mismatched.

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#5. Max Holloway vs. Chan Sung Jung – UFC Fight Night 225

Many fans are worried for Chan Sung Jung in his upcoming bout with Max Holloway [Image Credit: @ufc on Twitter]

The first bout on this list hasn’t actually happened yet, as it’s set to go down this weekend. It features two of the UFC featherweight division’s biggest names, but to say that Max Holloway and Chan Sung Jung aren’t on the same trajectory right now is an understatement.

The former featherweight champion, Holloway has been on the roster now for over a decade, but he looks to be in arguably his best-ever form.

If you ignore his three losses to current titleholder Alexander Volkanovski, he’d probably still have the gold around his waist. He’s dismantled the likes of Calvin Kattar, Arnold Allen, and Yair Rodriguez, and is amongst the best pound-for-pound fighters in the world.

Jung, on the other hand, has not fought since his own loss to Volkanovski well over a year ago. ‘The Korean Zombie’ reportedly considered retirement after that fight, and most fans believe that he’s past his prime.

It’s a belief that definitely makes sense. Not only is Jung 36 years old, but he’s also won just once since 2019. His legendary durability now appears to be on the wane, and he’s slower than he was in his prime.

Essentially, this looks like a complete mismatch in Holloway’s favor, at least on paper, and it seems almost unfair to put ‘The Korean Zombie’ in there with him. Of course, any fighter has a puncher’s chance, but it seems likely that this one will end badly for Jung this weekend.

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#4. Tito Ortiz vs. Patrick Cote – UFC 50

Tito Ortiz's 2004 bout with Patrick Cote was seen as a mismatch [Image Credit: @titoortizig on Instagram]

Back in 2004, despite back-to-back losses to Randy Couture and Chuck Liddell, Tito Ortiz was still considered one of the most feared light-heavyweights in the world.

The UFC clearly wanted ‘The Huntington Beach Bad Boy’ to rebound from his two defeats, and so they matched him with the aging Guy Mezger in the main event of the final pay-per-view of the year.

Unfortunately, Mezger ended up suffering a stroke in training and unsurprisingly, was forced out of the fight.

That left the promotion scrambling, and unable to get a high-level replacement in on short notice, they elevated debutant Patrick Cote, who was booked on the preliminary card, into the spot.

My Biggest ever "wtf, I can't believe they fought!" moment, Patrick Cote fought Tito Ortiz at UFC 50 by in MMA

Cote was 5-0 at the time and looked like a decent prospect, but despite talking a good game, nobody really gave him a chance against the former champion.

In the end, despite Cote stunning Ortiz in the first round with a right hand, the bout was indeed a mismatch and saw ‘The Huntington Beach Bad Boy’ dominate for a three-round decision.

Nobody was really harmed by the fight, as ‘The Predator’ went on to enjoy a solid career with the UFC, but all in all, it was a largely pointless mismatch despite its headline status.

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#3. Islam Makhachev vs. Bobby Green – UFC Fight Night 202

Islam Makhachev was given a mismatched fight with Bobby Green in 2022 [Image Credit: @ufc on Twitter]

Prior to his capture of the lightweight title in October 2022, Islam Makhachev was one of the world’s most feared 155lbers. However, the Dagestani often found it hard to pin high-level opponents down to face him.

Case in point was his headline fight at UFC Fight Night 202 in February 2022.

Initially, Makhachev was booked to face off with fellow top-ten-ranked lightweight Beneil Dariush at the event. However, when Dariush pulled out, finding a replacement for him seemed impossible.

Usually, plenty of fighters would jump at the chance to fight a highly-ranked foe, but Makhachev’s reputation preceded him, and so only one man stepped forward: Bobby Green.

‘King’ was coming off back-to-back wins, but he’d also lost a number of other fights and, at the time, wasn’t ranked anywhere near the top ten.

Essentially, the bout looked like a total mismatch on paper, and nobody was shocked when Makhachev took Green down and destroyed him with punches inside a round.

Sure, the fight was a late-notice one and the promotion did well to keep Makhachev on the card, but that didn’t make the matchmaking any fairer.

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#2. Conor McGregor vs. Dennis Siver – UFC Fight Night 59

Conor McGregor's second UFC headliner was a mismatch against Dennis Siver [Image Credit: @ufc on Twitter]

By the end of 2014, it was clear that Conor McGregor was the fastest-rising star that the UFC had seen for some time.

The Irish featherweight had reeled off four wins in the promotion, defeating Marcus Brimage, Max Holloway, Diego Brandao, and Dustin Poirier, and it seemed his hype train could not be slowed down.

Following his win over Poirier, a number of fans called for ‘The Notorious’ to be handed a title shot, but the problem was that he hadn’t really beaten a top-ranked opponent.

The promotion decided that the final hurdle for McGregor would see him fight in the headliner of a Fight Night event booked in Boston in January 2015.

However, rather than match him with Chad Mendes or Frankie Edgar, they instead booked him against Dennis Siver. At the time, the German was not ranked in the top ten and had only won one of his last three bouts.

Most fans figured the fight, which seemed like a mismatch, was a lay-up for McGregor. Sure enough, ‘The Notorious’ dispatched Siver in the second round.

The Irishman was indeed handed a title shot after the win – and went on to claim the gold – but this remains one of the most mismatched headliners in octagon history.

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#1. Georges St-Pierre vs. Matt Serra – UFC 69

Even though he won, Matt Serra's bout with Georges St-Pierre was seen as a mismatch [Image Credit: UFC]

It’s widely regarded as one of the biggest upsets in UFC history, but the truth is that on paper at least, Matt Serra’s famous welterweight title bout with Georges St-Pierre was a huge mismatch.

The two men were matched against one another in the headline bout of UFC 69 in April 2007, but their paths couldn’t have seemed much further apart.

St-Pierre had knocked out Matt Hughes to claim the welterweight title in late 2006, and prior to that, had run through top-ranked foes like Sean Sherk, BJ Penn, and Frank Trigg. He looked all set to have a long and dominant reign as champion.

Serra, meanwhile, had been given his title shot off the back of an unconvincing win over Chris Lytle. That win had come in the finals of TUF 4, a show that guaranteed a shot at the gold for the winner.

However, ‘The Terror’ had also never beaten a top-level foe at 170lbs, and was more renowned for his work in the lightweight division than anything he’d done as a welterweight.

Literally, nobody was giving Serra a chance. That’s why it was so shocking when he caught ‘GSP’ clean with a right hand to the temple in the first round, wrecking his equilibrium and ending his reign shortly after.

Sure, ‘GSP’ regained his title easily when the two men rematched a year later, but Serra etched himself into octagon legend with this win. His victory is still considered one of the wildest moments in MMA history to this day.