The Top 20 Upsets in UFC history

Over 250 events and thousands of fights later, here are the Top 20 upsets from the Octagon.
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Upsets have become a part of sports lore and whether it happens in the Super Bowl or the World Series, fans always jump up and pay attention when a huge underdog rises from the depths to defeat a storied favorite.

From rookie fighters being thrown to the wolves against far more experienced competition, to salty veterans of the sport, considered to be past their prime and on their last legs, the upset can happen to any fighter, at any time and against all odds.

It's part of the reason why the upset is such a revered moment in sports and so with that we will begin our countdown of the 20 greatest upsets in UFC history.

#20: Junior Dos Santos def. Fabricio Werdum at UFC 90

Following a successful career in Pride, Fabricio Werdum came to the UFC hoping to make his mark in the heavyweight division. He admittedly had a horrible debut when he lost to former champion Andrei Arlovski, but he quickly rectified that with wins over Gabriel Gonzaga and Brandon Vera. It was then that Werdum was matched up with a relative unknown by the name of Junior Dos Santos.

Nobody knew much about Dos Santos except he was 6-1 at the time with all of his fights taking place in Brazil. A minute and 20 seconds later, Dos Santos made his name. He punished Werdum the moment the fight started and he didn't let up until he landed the knockout blow. Dos Santos made one of the most impressive debuts in UFC history while also pulling off a major upset over a legit heavyweight contender.

#19: Pete Williams def. Mark Coleman at UFC 17

From UFC 10 through UFC 12, Mark Coleman was considered to be the best fighter in all of mixed martial arts. A bruising wrestler with unmatched power, Coleman was the kind of fighter all other competitors dreaded facing. If he got an opponent down, chances are they weren't getting up until the fight was over and Coleman's hand was raised.

Then in walked Lion's Den fighter Pete Williams. An unremarkable fighter by all accounts, Williams was mostly touted in his debut because he happened to be a training partner of UFC legend Ken Shamrock. Williams decided to make people remember him for a different reason. Williams was able to counter and evade Coleman's attacks all night during their fight and with time moving past the 12th minute it was clear the former UFC heavyweight champion was fading fast.

With his arms down at his knees as his lungs begged for oxygen, Coleman slumped over and Williams met him with a sickening kick straight to the face. Coleman dropped like a sack of potatoes as Williams became the first fighter ever to finish the former Ohio State All-American in the UFC.

#18: Houston Alexander def. Keith Jardine at UFC 71

If you knew the name Houston Alexander prior to UFC 71 you were probably related to him at the time. Alexander took a fight against former Ultimate Fighter competitor Keith Jardine just one fight after he knocked out Forrest Griffin inside the Octagon. It wasn't even a question of who would win, more about how did Alexander land this fight in the first place?

Well it turns out he was a bomb just waiting to go off because after a few heavy exchanges in the opening moments of the fight, Alexander got the upper hand and unloaded on Jardine with a series of strikes that buckled the New Mexico fighter's legs as he collapsed to the ground. It took Alexander just 48 seconds to beat Jardine and enter the record books as one of the most severe underdogs to ever come away victorious in the UFC.

#17: Joe Lauzon def. Jens Pulver at UFC 63

Jens Pulver returned to the UFC in 2006 after four long years away from the promotion. He was coming back with the premise being he would fight one bout and then face off against old rival BJ Penn to settle their long standing grudge.

Facing Pulver in his 'warm up bout' was a little known grappler from Massachusetts named Joe Lauzon. Of course Lauzon knew about Pulver's power and prowess, but none of it mattered in the fight. Lauzon battered Pulver the second the fight started until it came to an end just 47 seconds later. As it turns out, Pulver was headed to coach on the new season of the Ultimate Fighter opposite Penn and strangely enough Lauzon ended up on the show as well. He did get drafted to Penn's team, however, so at least Pulver didn't have to coach the man who just beat him in his return to the UFC.

#16: Rashad Evans def. Chuck Liddell at UFC 88

Chuck Liddell stepped into UFC 88 after the fight of his life when he finally faced and defeated Pride legend Wanderlei Silva in one of the greatest slugfests in UFC history. It was the kind of moment that define careers, and Liddell came out the victor. Now he had to face former Ultimate Fighter winner Rashad Evans with the winner getting the next crack at the light heavyweight title.

Liddell was on top of the world after the win over Silva, but it only took one punch for Evans to bring him back to Earth. Liddell controlled the first round and it looked like he was going to do the same in the second until Evans unloaded a right hand over the top that crushed the former champion's jaw as he dropped to the mat in emphatic fashion. A stunned crowd in Atlanta just sat shocked as Liddell was knocked out and Evans stood tall as the winner and new contender in the division. As it turns out, Liddell's win over Silva would actually stand as the last of his career before retiring in 2010.

#15: Carlos Newton def. Pat Miletich at UFC 31

In the dark days of the UFC when even pay-per-view stopped being a televised option, the promotion pushed forward while also adding some seriously talented fighters. One of them was very talented competitor named Pat Miletich, who won and defended the UFC welterweight title on four occasions when he was matched up with a Canadian grappler named Carlos Newton.

Newton was a medical student who was on his way to becoming a doctor, and Miletich beating this kid wasn't supposed to be anything challenging. Newton wasn't going away easy, however, and midway through the third round the slick grappler grabbed hold of a headlock squeezing and pulling at Miletich's neck. The pressure was too much and Miletich had to tap out. Newton was the new UFC welterweight champion and Miletich would only fight in the UFC two more times before exiting the promotion for good.

#14: Chris Weidman vs. Anderson Silva at UFC 162

The odds said that Chris Weidman was a real, legitimate threat to take Anderson Silva's title away from him after seven years atop the middleweight division. There were dozens of fighters who were picking Weidman to win, saying he had the perfect combination of standup and ground game to finally bring Silva down. Then again, maybe it was just wishful thinking on the part of a group of middleweight who just wanted no part of ever having to face Silva with the belt on the line.

Regardless of odds or predictions, Weidman was facing the greatest champion the UFC has ever known and it was a tall order to tackle. Still, Weidman wasn't backing down one bit in the face of Silva's typical in fight antics and during the second round when the champion was bobbing and weaving his head, inviting trouble, the former college wrestler gave it to him. Weidman clipped Silva's chin and sent him crashing to the mat. A few more strikes followed and Weidman had done the impossible — he finished Anderson Silva by strikes.

#13: Forrest Griffin def. Quinton 'Rampage' Jackson at UFC 86

Despite a win over Mauricio 'Shogun' Rua in his last fight, Forrest Griffin entered his bout against Quinton 'Rampage' Jackson like a dead man walking. Sure, he beat the former Pride Grand Prix champion but that was just a lucky performance. No way he could do that two times in a row, much less against the man who not only knocked out Chuck Liddell but just put on the fight of his career against Dan Henderson to become the first ever unified champion in the UFC.

Maybe it was motivation, or lack there of, or maybe it was just the wrong night to be off his game, but Jackson failed to get his motor running against Griffin over the course of five rounds. Griffin targeted Jackson's lead leg with kicks, and ended up using his thighs and calves like a soccer ball just destroying any chance 'Rampage' had of stepping forward with any real momentum. The champion kept it close but when it was over Griffin's hand was raised in victory as he became the first Ultimate Fighter winner to take home UFC gold.

#12: Keith Jardine def. Chuck Liddell at UFC 76

Chuck Liddell needed to get a win after being knocked out by Quinton "Rampage" Jackson for a second time while losing his UFC light heavyweight title along the way. If the UFC was ever going to try and pit Liddell against Rampage again, he needed to get a few dominant wins to step back into the title picture. So he was matched up with former Ultimate Fighter season 2 competitor Keith Jardine. At the time, Jardine was just off of another huge upset loss to Houston Alexander, and never seemed like a major threat to Liddell.

If anything he was going to give Liddell the highlight reel knockout he needed so people could forget what happened in the Rampage fight. Somebody forgot to tell Jardine that he was supposed to just roll over and die, and he ended up butchering Liddell's legs and midsection with kicks over the course of three rounds leaving 'The Iceman' battered and bruised. The judges returned a split decision when it was over, but anybody watching the fight knew that Jardine was the clear winner, and he sent Liddell packing back to the end of the line trying to figure out what went wrong.

#11: Frankie Edgar def BJ Penn at UFC 112

BJ Penn was the lightweight champion the UFC had always been waiting for since reintroducing the division in 2006. He was charismatic, talented and a hurricane inside the Octagon that drew in fans from all over the world to buy any pay-per-view he was taking part in. So when he faced off against quiet New Jersey boy Frankie Edgar, this was supposed to be just another day at the office for Penn, who had already blown through top contenders like Sean Sherk, Kenny Florian and Diego Sanchez.

Once he got in the Octagon with Edgar though he found out what a real challenge felt like. Edgar's boxing was crisp and fast, and when he mixed in his wrestling Penn had to keep guessing at which attack would come next. When it was over, the judges awarded a unanimous decision victory to Edgar and that would be the last time Penn would see a title in his UFC career (up until now anyways).

#10: Randy Couture def. Chuck Liddell at UFC 43

Randy Couture is a name you'll get used to seeing on this list. No matter how good Couture was during his career, he seemed to keep popping up in impossible situations with the odds stacked firmly against him.

Thus was the case when Couture moved down to 205 pounds after suffering losses to both Josh Barnett and Ricco Rodriguez that forced him out of the heavyweight division. Couture was matched up with knockout artist Chuck Liddell, and it was assumed the moment the fight was made that the old man was about to get a very rude welcome to the division courtesy of 'The Iceman'.

Couture had other ideas and decided to out box, out wrestle and just out fight Liddell at every moment they were in the cage together. Finally after a dominant first 10 minutes, Couture put a stop to the fight by TKO in the third round capping off one of the most incredible upsets ever witnessed in the UFC.

#9: Tito Ortiz def. Ryan Bader at UFC 152

Despite a long, successful career that saw him win and defend the UFC light heavyweight title more than any fighter in UFC history (at the time), Tito Ortiz's run came to a dramatic halt starting in 2006 when he was knocked out for a second time by his old friend Chuck Liddell. From that point on, Ortiz wallowed in a sea of misery going 0-3-1 during that time and with losses mounting, it appeared his UFC career was almost at its end.

Before he left, however, the UFC gave Ortiz one last shot at redemption against former Ultimate Fighter winner Ryan Bader. On paper the matchup was horrible for Ortiz. Here was a young, hungry wrestler who did everything Ortiz did except better. Still the former champion was determined to save his career for another day, and after stunning Bader with a short punch early in the fight, Ortiz jumped up and grabbed a guillotine choke, pulling the fight to the ground.

Bader had no where to go and was forced to tap out at 1:56 in the first round. Ortiz celebrated and felt renewed after not only saving his job but reminded everyone why they shouldn’t count out 'The Huntington Beach Bad Boy' ever again.

#8: Randy Couture def. Vitor Belfort at UFC 15

Through the first few fights of his UFC career, Vitor Belfort looked like an unstoppable killing machine. He crushed four opponents in a row — the last of which happened to be legendary street fighter and UFC fixture Tank Abbott in just 52 seconds. Belfort was the closest thing the UFC had seen to Mike Tyson at that point, but just like the boxing champion eventually someone like Buster Douglas had to come along and in this promotion his name was Randy Couture.

A former wrestler who didn't start fighting until he was almost in his mid-30's, Couture was supposed to be just another notch on Belfort's hit list until they actually fought against each other in the cage. Couture beat Belfort and exposed him in ways no one had come close to doing before.

At just over eight minutes into the fight, Couture put Belfort down once and for all and walked out a winner that night but unlike Douglas in boxing, he became a legend and one of the greatest fighters of all time throughout his storied career.

#7: Forrest Griffin def. Mauricio 'Shogun' Rua at UFC 76

Mauricio 'Shogun' Rua came into the UFC from Pride Fighting Championships with as much hype as any fighter had ever felt in their Octagon debut. He was long thought to be the uncrowned champion of his former promotion in Japan, and the talent he showcased when blasting through fighters like Quinton 'Rampage' Jackson and Ricardo Arona made him a very popular person on day one in the UFC.

The unfortunate soul who was sent to greet the grim reaper as he arrived at the Octagon door was former Ultimate Fighter winner Forrest Griffin. He was the unlucky soul that the UFC offered as a sacrifice to the alter of Shogun. Except, Griffin wasn't ready to unlock the door and hand over the keys to the kingdom and after wearing out Shogun in a bloody battle through the first 10 minutes, he finally seized his moment in the final round.

With Shogun's gas tank nearly depleted, Griffin sunk in a rear naked choke and got the tap out from the Brazilian. An elated Griffin did laps around the cage as he celebrated a huge moment in his career, and one of the biggest victories he'd ever experience as a fighter.

#6: Randy Couture def. Tim Sylvia at UFC 68

When Randy Couture lost to Chuck Liddell for a second time and announced his retirement that was supposed to be it on what was already a historic career. The moment Couture announced he was coming back less than a year later wasn't necessarily shocking, but when we learned that it was going to be at heavyweight where he would face 6'8" champion Tim Sylvia, we all believed he had gone crazy.

Couture knew exactly what he was doing an in front of 19,000 plus fans at the Nationwide Arena in Columbus, OH, the legend rose again. Couture beat Sylvia to the punch on the feet and then wrestled the giant to the ground time after time until the fight ended. Couture was proclaimed the victor by lopsided decision while he took home yet another UFC title to add to his collection.

#5: Jens Pulver def. BJ Penn at UFC 35

This selection could easily be flipped with No. 4 and ironically both involve UFC legend BJ Penn. In 2002 when the UFC was just getting adjusted to life under new owners Lorenzo and Frank Fertitta along with president Dana White, the lightweight division was an open weight class with no defined No. 1 fighter.

One person stood above the crowd, however, and that was a lightning fast and devastating fighter named BJ Penn, who debuted a year earlier and absolutely decimated three fighters in a row before being matched up for a title shot against Jens Pulver. The fight was a formality — Penn would win and hold the lightweight title for years to come and Pulver would just be a speedbump in the road. The only problem is no one bothered to tell Pulver that news, and he proceeded to put on a masterful five round performance to beat Penn, win the UFC lightweight title and hand the Hawaiian his first professional loss. The win still stands as the biggest of Pulver's career and one of the most memorable upsets to ever happen in the UFC.

#4: BJ Penn def. Matt Hughes at UFC 46

There was no denying BJ Penn's talent from the first day he stepped foot in the UFC, but no matter how close he got the Hawaiian prodigy just couldn't capture lightweight gold. Time after time whenever Penn got close, the belt got snatched away from him.

So when Penn decided to move up to welterweight to challenge incumbent champion Matt Hughes for the belt, just about everyone thought the much smaller fighter was about to get a rude welcome to 170 pounds. Instead, Penn came out blazing and caught Hughes early before wrapping him up for a rear naked choke to end the fight in the first round. Penn ended Hughes' reign as champion in emphatic fashion once again proving that it's not always the size of the man in the fight, but the size of the fight in the man.

#3: Royce Gracie winning UFC 1

Now we can all look back and talk about how the UFC was founded by the Gracie family as an exhibition to show what Brazilian Jiu-Jitsu was all about, and Royce Gracie was their ringer to go in and destroy the competition and win all the money and tournament glory.

But at the time, nobody was looking at tall, lanky Royce Gracie as a threat to some of the physical monsters that stepped foot in the Octagon that cold night in Denver in November 1993. It was an incredible sight to watch Gracie, time and again, pull his opponents to the ground, wrap them up like an anaconda does to its prey, and second later land the fight finishing submission hold. It took Gracie all of four minutes, 59 seconds to dispatch of three separate fighters including future UFC Hall of Famer Ken Shamrock among them to win the first ever UFC tournament.

He went on to win two more UFC tournaments and is still widely regarded as one of the greatest fighters of all time but the first time he stepped in that cage there certainly weren't many people on the outside looking in that expected him to win.

#2: Gabriel Gonzaga def. Mirko Cro Cop at UFC 70

When Mirko Cro Cop came to the UFC by way of Pride Fighting Championships, he was supposed to be the heavyweight champion inside of approximately three fights. He needed one warm up bout to get introduced to the American crowd, a second to become the No. 1 contender and then a third to finally get the gold.

The problem was for his second bout he was matched up against tough Brazilian fighter Gabriel Gonzaga, who had no intention of laying out the red carpet for Cro Cop on his path to the belt. Gonzaga was undefeated in the UFC at the time, and he showed absolutely no fear facing Cro Cop in the heavyweight showdown.

In fact, when the opportunity presented itself, Gonzaga launched a high kick at Cro Cop's head, which just so happened to be his signature move. Gonzaga's foot crushed the Croatian's head, and as he flopped to the floor and the entire world sat there with mouths gaped open and eyes as wide as the moon, the legend of Cro Cop died while witnessing one of the biggest upsets to ever happen inside the Octagon.

#1: Matt Serra knocks out Georges St-Pierre at UFC 69

For the biggest part of Matt Serra's career he was MMA's equivalent of a' knockaround guy'. He was part of the gang, but never ascended to the top levels of the organization. Serra came close to lightweight glory when he lost a controversial decision to BJ Penn at UFC 39 in 2002, but outside of that he was always a middle of the road fighter that never quite captured greatness.

Serra was even released from the UFC at one point and had to earn his way back during a stint on The Ultimate Fighter season 4 dubbed 'The Comeback'. Serra had to go through a group of fellow welterweights all hoping to earn a title shot as the reward for making it through the show and getting another crack at the UFC. Serra won the show by defeating former housemate Chris Lytle in the finals, but he was then pitting against Georges St-Pierre for the UFC welterweight title.

St-Pierre was everything right about MMA — he was young, good looking athletic and a freak of nature that absorbed every facet of the sport like a sponge, getting better and better with each fight. He was supposed to be the next great champion — that was until April 7, 2007 when he met a scrappy kid from New York named Matt Serra.

Following a few sloppy exchanges between the two fighters, Serra uncorked a huge punch that wobbled St-Pierre and immediately the 10 to 1 underdog pounced on his prey. Serra unloaded shot after shot after shot until St-Pierre wilted and eventually tapped out due to strikes. Serra jumped up with a huge smile on his face as he pulled off the impossible and knocked out St-Pierre to win the UFC welterweight title in undoubtedly the biggest upset in UFC history.

Click here for more Top 20s honoring the UFC's 20th Anniversary

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