City Kickboxing's Adesanya has defeated the likes of Derek Brunson, Robert Whittaker, Marvin Vettori, and more as he makes a run for one of the greatest champions in UFC history. Though he'll be defending his Middleweight title against Jared Cannonier, Adesanya will be near a familiar foe during international fight week.

Israel Adesanya landing a right hook against Jason Wilnis in Kickboxing. Credits to: James Law-GLORY Sports

Before he transitioned to MMA full-time in 2017, ‘The Last Stylebender’ was an accomplished kickboxer, amassing a record of 75-5 over the course of his pro career. He competed in China as well as New Zealand, capturing titles and knockouts en route to competing in Glory Kickboxing, the world’s premier kickboxing promotion. It was in Glory where the UFC Middleweight Champion would run into his biggest rival for the first time– Alex ‘Poatan’ Pereira.

Alex Pereira finishing Thomas Powell by knockout. This was his final win in MMA before joining the UFC. Credits to: Jerry Chavez-LFA

Pereira and Adesanya fought for the first time in a three-round bout at Glory of Heroes 1: Shenzhen, where Pereira would capture a unanimous decision victory. The two would then rematch a year later at Glory of Heroes 7 in Sao Paulo, Brazil, with differing results for both sides. The reigning UFC Middleweight Champion would see a lot of success in the rematch, winning many of the exchanges.

He kept the Brazilian on the back foot, peppering him with combinations, nearly finishing Pereira with a standing knockdown in round two. When it seemed like he was on his way to avenging the first loss to Pereira, Adesanya’s success would come to a screeching halt when he was brutally knocked out by a picture perfect counter left hook to the chin in round three.

At the time of writing this, that remains the only time Adesanya has been knocked out in his illustrious combat sports career. After the win, Pereira would go on to become Glory’s first two-division champion, capturing the Middleweight and Light Heavyweight titles. The loss would also be the final kickboxing bout of Adesanya’s career before he transitioned to MMA.

Like his former adversary, Pereira would make the transition to MMA from kickboxing in the mid-2010s, however, it was not until 2021 that he would be signed by the UFC. Holding a record of 3-1, he made his debut in November of 2021, capturing a flying knee knockout win over Andreas Michailidis at UFC 268: Usman vs. Covington 2, earning him a performance of the night bonus. His sophomore fight in the UFC came against Bruno Silva where he would win a unanimous decision. The first two rounds were competitive, but Pereira came on strong in the third to take the victory.

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At this point, it became clear that in a depleted Middleweight division, fast-tracking the kickboxing champion towards another fight with Adesanya would be the best promotional choice the UFC could make. Not only does he hold two wins over the current champion, but he also is an action fighter with massive power in his hands.

In what will easily be the most difficult test of his career, Pereira is set to take on Sean Strickland at UFC 276 at the T-Mobile Arena in Las Vegas, Nevada. This is just two fights down the card from ‘The Last Stylebender’s’ latest title defense. If each picks up a victory Saturday night, it seems clear that the trilogy fight for the UFC Middleweight Championship is the fight to make. Whereas the first two fights were in the kickboxing realm, the third fight would be in the mixed martial arts realm.

If Israel gets past Cannonier, which is a difficult task in its own right, the division will lack fresh contenders for the Champion, outside of the winner of Strickland and Pereira. As well, Pereira is 34 and has not had the same amount of time to develop a well-rounded MMA game, meaning matching him up with the elites of the Middleweight division is a risky game.

Currently, 52% of the Verdict Community is picking Pereira to get it done on July 2nd, which means another 0-2 trilogy bout could be coming sooner than we may think. Only this time it would take place in the Octagon, in an entirely different sport. Kickboxing isn’t MMA, and MMA isn’t kickboxing, but this rivalry transcends disciplines and would be a massive part of the legendary history between these two fighters.

Since International Fight Week - July 2022

Ahead of UFC 276: Adesanya vs. Cannonier, the direction was clear. ‘The Last Stylebender’ would rattle off his fifth title defense and then look to make it six against the winner of Sean Strickland and Alex Pereira, which was happening just two fights down the card from the championship main event.

Israel Adesanya was able to defend his title against a defensive but game Jared Cannonier, which ultimately set up the matchup fans and promoters alike had been clamoring for. Around an hour before Adesanya made the walk, Pereira had iced Strickland in the first round—with the same patented left hook that had stopped Adesanya in 2017.

By the time the broadcast had ended, everyone knew what was next, and just five months later, UFC 281: Adesanya vs. Pereira took place at Madison Square Garden in New York, NY in November 2022.

The build-up was big. By the time the fight got closer, even the most casual MMA fan knew that ‘Poatan’ had gotten the better of Adesanya in the past in kickboxing. The weight of what a third loss would mean for the champion was evident leading in, and there was excitement as Pereira was perhaps the most dangerous opponent Adesanya had faced in some time.

The first MMA fight between Adesanya and Pereira

The third fight between the two kickboxer-turned-martial artists was much like the last two—incredibly close and ultimately ending in the same result.

Their first UFC round belonged to Adesanya. After a close round, ‘Stylebender’ caught Pereira with a solid right hand and follow-up left right at the horn. ‘Poatan’ was rocked. Enough so, that there were questions if he would recover in time for the next round.

Entering the second, Pereira had recovered and was the aggressor. He kept the champion on the backfoot and even landed a takedown in the closing moments of the round. All three judges had it 19-19 entering the third.

The third was a clear ‘Stylebender’ round after he scored a takedown around the 3:40 mark and racked up 3:47 of control time along with some strong ground and pound.

The fourth also ended up being a 10-9 win for the defending champion after he got the better of ‘Poatan’ on the feet and controlled the clinch.

Just like their second matchup in Glory, Adesanya was leading on the scorecard. Pereira needed another come-from-behind knockout—and that’s what he got.

Alex Pereira landing the left hook that's haunted Israel Adesanya. This was his final win in MMA before joining the UFC. Credits to: Jeff Bottari/Zuffa LLC

Around the three minute mark, that dreaded left hand landed, wobbling the champion badly. From there, Pereira brought on a storm of devastating shots until, eventually Marc Goddard was forced to step in and prevent the inevitable destructive knockout that was coming for Adesanya.

A dominant title run had ended at the hands of a rival from another sport. Pereira had come to the same promotion and was fast-tracked to the title shot. Of course, he executed at every stop to continue to get the opportunities, but the title run was abrupt. And still, just like the first bout, he maybe should have won and the second where he was leading before the stoppage, Adesanya couldn’t get over the hump against Pereira.

However, the story between these two champions is still not yet fully written despite the 3-0 score. The two will rematch and fight for the second time in MMA in the main event of UFC 287: Pereira vs. Adesanya 2 on April 8, 2023.

There is much at stake entering this fight and also so many unprecedented outcomes that could come out of it. If Pereira wins, let alone by stoppage, he’ll have four wins over Adesanya with two coming in each sport. Inevitably, Adesanya would be more a part of Pereira’s story and would be thrown back into the mix as a contender that has to defend his ranking—something we haven’t truly seen since 2019. Regardless of his past brilliance, two losses to Pereira would be a blip on the record of Adesanya that would be hard to look past. If ‘Stylebender’ can win his title back, he’ll be right back on the path toward historical greatness.

And for ‘Poatan’, he could cement himself as one of the stranger and more unexpected Middleweight greats in recent memory yet also a target for contenders who may be a difficult style matchup for the Brazilian. There is also a lot of discussion around him moving up to Light Heavyweight, especially if Jamahal Hill retains his newly found title.

On a loss, ‘Poatan’ would be a former champion entering a pool of contenders that might be favoured over the striking specialist. It would be interesting to see how he does against the likes of Robert Whittaker,

Despite the matchup being a “quadrology” or rematch based on how you see it, this fight feels fresh. The division is in new hands perhaps just for the moment, but Middleweight history is still in a very interesting place entering that April fight.

Israel Adesanya's Revenge

That was the important question entering UFC 287: Pereira vs. Adesanya 2 that would ultimately swing the result of the fight and define a historical rivalry. What would have to change for Israel Adesanya to finally beat Alex Pereira for the first time in four fights across two combat sports?

As it turns out, not much did change outside of the result, which is what made Adesanya’s stunning second round knockout of Pereira all the more impressive.

Like the last two matchups prior to Saturday’s contest, and even their first matchup in kickboxing all the way back in 2017, the man who ultimately won the fight was on their way to losing before the tide turned in the other’s favour.

Saturday’s bout started dead even with both men finding the target with potent leg kicks while they felt each other out. Pereira then began to take control as the second round went on. He looked to have hurt ‘Stylebender's’ leg and began landing menacing strikes along the fence, so much so that a finish for Pereira didn’t seem like it was all that far away.

As Pereira landed menacing shots along the fence, Adesanya countered beautifully and found a home for the exact same right hand that nearly finished Pereira at the very end of round one in their first MMA fight last November—only this time there was enough time left on the clock to capitalise.

After wobbling ‘Poatan’ with the first punch, Adesanya landed a follow-up of the exact same punch that slept the champion, sending him crashing to the canvas and the belt back to City Kickboxing where it had stayed since 2019.

It’s difficult to put into words the magnitude of Adesanya’s victory Saturday. Everything was on the line. Lose, and he’d be 0-4 against Pereira across two sports including being knocked out at least twice. Lose, and he’d be sent back into the pool of contenders without a true direction as to what would be next. Lose, and he’d have two losses to his archrival as a stain on an otherwise near-flawless Middleweight career.

But Adesanya wouldn’t be denied Saturday in Miami.

It isn’t just the fact that Adesanya finally got the better of Pereira, it’s the way he did it. The knockout is likely an early knockout of the year contender given its brutality, the stage and the context between the fighters, but it is also the greatest win in a career full of them for Israel.

Overcoming an opponent like ‘Poatan’ is incredibly difficult no matter the circumstance, but to come back and win by devastating knockout in an immediate rematch to reclaim the title after being finished is even more impressive. Pair the KO with a tremendous in-ring-celebration and post-fight interview and Adesanya created yet another viral moment for MMA fans.

In terms of what’s next in the immediate future, that’s where things become far murkier. With wins over every contender in the top five, the division lacks a clear contender for the now two-time champion. Adesanya shot down the idea of an immediate MMA trilogy with ‘Poatan’ and most signs point to the Brazilian moving up to Light Heavyweight, leaving a large hole in the top of the division. But a fifth fight wouldn’t be the worst choice by the UFC given how close each of the four matchups have been and given the lack of depth in the division.

Dricus Du Plessis might make the most sense for Adesanya when it comes to a fresh matchup, but he currently sits at #6 in the rankings and needs another high quality top five win to be fully deserving of a title shot.

For ‘Poatan’, it seems like a move to 205 pounds is imminent. He’ll be a tough matchup for whoever he faces and could make a splash in the Light Heavyweight title picture as a former champion and another gifted striker in a top five full of them.

Now that it’s over, the discussion turns to what UFC 287 means for the legacy of both of these men and their rivalry. Although Pereira got the better of the four matchups, taking three, it’s impossible to say that the rivalry wasn’t razor thin, and tough to say that Adesanya’s lone win wasn’t the most impressive.

Pereira was Middleweight champion for just 147 days, and as time goes by, some may look at his time at the top as a flash in the pan. However, what he did to capture the title from Adesanya in the first place can’t be forgotten and should be celebrated for the incredible moment it was and forever will be. His transition from kickboxing to MMA was almost as rapid as his ascension up the rankings and to the title, and regardless of what happens next, Pereira’s MMA career is one of the most unique and captivating in recent memory.

For Adesanya, the win gives the champion his eighth title fight victory and he is now the only two-time champion in Middleweight history. It also puts him in an elite group of champions who were able to win their belt back while avenging a loss—something MMA fans value greatly when comparing champions historically. The win also puts Stylebender’ back on the path to potentially becoming the greatest Middleweight champion the UFC has seen, though he definitely has some work to do to catch Anderson Silva.

Regardless of what you think about either man, the level of technical ability mixed with mental warfare and drama has made this rivalry that started in kickboxing one of the most intriguing in MMA history.

No matter what happens next for the two men, their incredible career stories are inherently intertwined forever in the history of combat sports.