Matt Serra defeats Georges St-Pierre in one of the greatest upsets in UFC history

When Anthony Smith received his title shot against Jon Jones, fans applauded politely. Smith put on a gutsy performance against Volkan Oezdemir, but no one believes he has a shot at beating Jones. But in the unlikely event that he does beat Jones… where would it rank among the UFC’s biggest upsets?

Two notes before we get into the list.

  • There is a difference between the “greatest” upset and the “biggest” upset. Greatest is subject to historical context and fan favoritism while measuring the sheer scale of the upset is not.
  • We consider both odds going into the fight and pundit analysis. As you know, there are many fights in which the odds do not reflect fan or expert opinion.

For example, Nate Diaz beating Conor McGregor on short notice is considered an upset. But Nate was the biggest fighter Conor had ever fought, and he faced a height and reach disadvantage for the first time in the UFC, the Irishman plausibly crumbled. So despite a huge fan reaction, the fight didn’t make this list.

Honorable Mentions:

  • Amanda Nunes def. Cris Cyborg
  • Frankie Edgar def. BJ Penn I
  • Fabricio Werdum def. Cain Velasquez

5. Holly Holm def. Ronda Rousey/Chris Weidman def. Anderson Silva I

Starting off the list, we have a pair of upsets that are nearly identical in what they represent.

Both Rousey and Anderson stomped their respective divisions. In their primes, both were the face of the UFC. And both of them saw a fall from grace arguably unmatched by any other UFC ex-champions. So why are they so low on the list?

Well, as I’ve stated in the case of Holm vs. Rousey, a lot of knowledgeable pundits and fans believed the upset was plausible. In Rousey’s case, Holm was the best athlete and striker she’d faced in a threadbare division. Before the Weidman upset, reliable fighters and pointed out that the American was a stylistic nightmare for Silva (they were right).

So while these upsets are significant in UFC history, the actual magnitude is much lower.

4. TJ Dillashaw def. Renan Barao I

There was no way to see this coming, because the TJ Dillashaw that stepped in against Renan Barao was a different fighter.

For a long time, Dillashaw existed as a typical boxer/wrestler hybrid. He came into UFC 173 with an 8-2 record, splitting his last two fights. Considering the opposition Barao embarrassed, people had little faith in a man who’s most recent win was a unanimous decision over Mike Easton. As it turned out, a different man stepped into the ring.

Against Barao, Dillashaw morphed into an unbelievable striker. He faked, dodged and countered Barao’s increasingly panicked haymakers. Instead of attacking him head-on, he constantly shifted stances and sidestepped to find angles. If Barao’s defense was a colander, Dillashaw’s fists and shins was a steady stream of water. It is not an exaggeration to say that Dillashaw became twice the fighter he was before seemingly overnight.

And it wasn’t a fluke either, because Dillashaw is now the greatest bantamweight in history.

3. Rose Namajunas def. Joanna Jedrzejczyk I

The same as #4, but even better.

Young and hungry, Rose Namajunas didn’t impress in her early fights. The fact she got a title shot with a 6-3 record and splitting her last two revealed the lack of depth at women’s strawweight. The loss came against Karolina Kowalkiewicz, a fighter that lost to the champion already. Conversely, Joanna Jedrzejczyk was a multiple-time world champion kickboxer and undefeated. With all due respect to the strawweights of the time, Joanna looked like an actual championship caliber fighter in a division full of good athletes with rudimentary skills.

Then Rose came out and pasted her in one round. Nothing indicated that the woman who submitted the comparatively diminutive Michelle Waterson. And yet her razor-left hook dropped Joanna in the fight’s opening action. As though to silence anyone doubting it as a fluke, Rose stepped in deep with another left which this time put Joanna down for good.

The young, athletic girl with rudimentary skills evolved into a terrific power striker with no warning.

2. Michael Bisping def. Luke Rockhold II

Now we get into challengers who, even after winning, were the provably inferior fighter.

For the longest time, Michael Bisping was the bridesmaid instead of the bride. Good enough to beat talented middleweights, he fell short against title-caliber opposition. Sometimes, it was a questionable decision such as his decision loss to Chael Sonnen. But many times, fighters simply outclassed him.

He’d made incremental improvements to his game over the years. He developed a decent left hook, didn’t run straight backward after every exchange and could actually hang in exchanges. But he still nearly lost to a geriatric Anderson Silva. So when he filled in for Chris Weidman on two weeks notice to rematch Rockhold, few had faith.

A few years ago, Rockhold was the best middleweight on Earth. Other than a setback against the TRT-infused Vitor Belfort, the lanky Californian had dissected every UFC opponent including Weidman.

Bisping did better; he didn’t run into check hooks and he baited Rockhold into missing several times. But he still couldn’t reach Rockhold with his power punches, and the few body kicks he ate visibly pained him. But then Rockhold stepped too deep on a missed jab and tried to pull straight back like he did every other time.

Except Bisping’s left hook caught him on the chin perfectly. Rockhold never recovered and went to sleep seconds later. It wasn’t a lucky punch; Bisping was aiming for that sort of collision whenever he threw his left over the top. But it was the best punch he’d landed in his entire career, and would land since.

On short notice, the rightful underdog found the perfect shot to take out a fighter he had no business beating.

1. Matt Serra def. Georges St-Pierre

Georges St-Pierre is, without a doubt, the greatest welterweight in history. Depending on how you view  Jon Jones’ drug tests and Anderson Silva’s quality of opposition, he may be the greatest MMA fighter ever. His record clocks in at an outstanding 26-2. Matt Hughes had the luck of catching St-Pierre in his eighth professional fight, well before his best. But the second loss? No one saw it coming.

By UFC 69, GSP was 13-1. His final win came via head kick over Matt Hughes to take the belt, avenging his only loss. Matt Serra, on the other hand, split his last six fights and fought four of those at lightweight. He gave up height, reach and speed and the only reason he got the fight was because he won the TUF 2 tournament.

At 5-foot-6 with a 69-inch reach, Serra was on the small side even as a lightweight. At welterweight, GSP dwarfed him almost comically. The NY native found himself at a disadvantage in height, reach, agility and talent. Plus, he’d only finished one opponent in the UFC and that was five years ago. There was no plausible way for him to win.

Keyword: Plausible

As GSP used superior footwork and striking to do what everyone expected him to do, Serra kept swinging at the Canadian’s ribs with his right hand. They weren’t anything to write home about, but GSP couldn’t just ignore them. Even if he won the striking exchanges, he had no intention of taking Serra’s power hand to the body repeatedly. So three minutes into the fight, Serra stepped in for a right hand and GSP lowered his guard.

Except Serra was aiming for his head.

It caught the champion behind the ear and Serra swarmed him. His short reach let him pump out right hand after right hand all of which landed and hurt GSP. Just 30 seconds after the miracle punch, a right caught GSP squarely on the chin and the rest is history.

Serra never recaptured the magic of that night. He couldn’t. GSP crushed him in the rematch and he retired off a 1-3 skid. Have them fight 20 times and GSP would win 19 of them. But somewhere in there, a short and proud New Yorker caught lightning in a bottle.

So, if Anthony Smith manages to beat Jon Jones where would he make it on this list? Stick around for part 2 to find out!

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