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Top 20 Biggest Upsets In MMA History

June 21, 2011 By: Category: Sports, UFC | Mixed Martial Arts

I don’t think it gets much more exciting in MMA than seeing a big upset. There is something about seeing an upset that electrifies a live crowd and can put you on the edge of your couch at home in seconds. Today I look back at twenty of the biggest upsets in MMA history.

All of these upsets were based on odds and reputation coming into the fight. Yes, in hindsight years later some of these wins weren’t exactly big upsets after all. However, at the time the handicapping of the fight prior to the event told a much different story. It is hard to believe seeing Tim Sylvia fight today that anyone would consider the loss to Randy Couture an upset, however the MMA community thought much different at the time as an example of what I am talking about.

So today in no particular order I go back through relatively recent history in and outside of the UFC and take a look back at some of the most exciting MMA upsets history. Keep in mind that I am putting these fights in no particular order of importance because let’s face it, an upset is an upset no matter how big or small the win is.

One last thing. Keep in mind how some of these fighters rebounded after their upset loss. Some came back stronger while others like many on the list never recovered. As big as the win is for the underdog, the loss could be absolutely traumatic for the loser and I think that is why we love upsets so much in MMA.

Joe Lauzon knocks out Jens Pulver September 23, 2006 - The home coming for Jens Pulver turned into a star-making night for his counterpart. Pulver was returning to the UFC for the first time in over four years and this fight was meant to be a showcase for the former champion. Instead, Pulver was looking up at the lights 0:47 seconds later.

Forrest Griffin chokes out Shogun Rua September 22, 2007 - Rua came in with all of the videos and hype from Pride FC. The UFC 76 odds had Griffin as a +250 underdog to Rua who was a -300 favorite. Rua came out strong early but Griffin held his own and gained confidence throughout the fight. Rua cut Griffin badly in the second round from an elbow but Forrest continued to fight back. Rua appeared to be gassed by the middle of round two and started to fade. Griffin came out inspired in the third round and caught Rua with a rear naked choke for the win with less than a minute to go in the fight for the upset.

Randy Couture defeats Chuck Liddell via TKO June 6, 2003 - Chuck Liddell had been blowing through the competition and was due a UFC light heavyweight title shot at Tito Ortiz. Instead of fighting Liddell, Ortiz left the UFC as champion to make a movie. Needing a big name and an easy win for Liddell, the UFC looked to Randy Couture. Couture moved down for the first time in his career after it appeared that the heavyweights were just too big for Captain America. With Ortiz in limbo, the UFC set up an interim title match and what was supposed to be the official crowning of the Iceman.

This fight was set up for Chuck Liddell to win and I don’t think anyone in their right mind expected Couture to even hang with Liddell, who had accumulated 10 straight wins. The Iceman was coming off a first round knockout win over Renato Sobral against Couture’s two straight losses at heavyweight. Couture was also just days away from his 40th birthday.

Couture did what no other man was able to do in the UFC against Liddell and that was take him down at will. Couture would smother the Iceman with takedown after takedown frustrating the heavy handed light heavyweight. Couture also won the striking battle against Liddell. Whether it was frustration or exhaustion, Liddell was getting just as outclassed on his feet as he was on the ground. The Natural eventually opened up an onslaught of ground and pound on Liddell in the third round that wound up ending Liddell’s 10-fight win streak

Nick Diaz taps out Takanori Gomi February 24, 2007 - After four years in the UFC, Diaz left the company for Pride Fighting Championships. Pride FC wasted no time putting together one of the most anticipated fights in MMA between Diaz and lightweight champion Gomi in a non-title fight.

Diaz was a heavy underdog with +317 odds to Gomi’s +347 odds. The fight was arguably the 2007 Fight of the Year with just brutal back and forth action. Gomi got a quick take down early but it was a different fight when they went to their feet. Diaz just peppered Gomi on the back and forth attacks with an onslaught of strikes. The end of the first round saw Gomi looking desperate and confused as Diaz walked back to the corner confident and cocky.

The second round saw Diaz come out fired up. Takanori Gomi opened up a cut under Diaz’s eye that saw blood pouring out of the face of Diaz. It got so bad that the ringside physician had to step in and examine Diaz. Diaz was cleared. After being dominated in the stand up game, Gomi took Diaz down. Unfortunately Gomi wound up in Diaz’s guard and shortly thereafter was tapping out to a Gogplata in one of the most exciting fights in Pride FC history.

Unfortunately Diaz showed up positive for marijuana in the pre-fight drug test and the fight was later ruled a no-contest.

Robert Berry knocks out Ken Shamrock on March 8, 2008 - Who, yes that Robert Berry..wait a second who? The MMA community knew that Ken Shamrock was done after being battered by Tito Ortiz in two straight fights, although Shamrock never got that memo. Shamrock’s first fight outside of the UFC was supposed to be one of his many comebacks. The only place that Shamrock came back to was the loss column.

Arguably Shamrock’s lowest moment came when he was knocked out by a journeyman MMA fighter at Cage Rage 25. The fight was stopped and Berry was awarded a TKO win 3:26 into the first round against the former WWE intercontinental champion. Shamrock went into the fight as a -220 favorite.

Frank Mir submits Brock Lesnar February 2, 2008 – This was Lesnar’s UFC debut and let me tell you, the UFC weren’t shy about promoting Lesnar’s WWE past. A collection of WWE stars right out of Legends of WrestleMania were show in the building throughout the night building a WWE vs. UFC theme for the fight. Lesnar was even announced as a former WWE champion with old wrestling footage to boot. It was certainly quite a spectacle indeed.

What I remember most about this fight is that in the weeks leading up to it and in my writings on phillyburbs.com I never believed Lesnar could beat Frank Mir. I thought Mir was too experienced here and that Lesnar would go into the fight over confident. I remember getting into several arguments with callers on my radio show about it, yet I didn’t think it was a huge revelation. Well, in this case I was right.

Lesnar bull rushed Mir and opened up with the same ferocity he unleashed against Kim. Lesnar dropped Mir pretty quickly and the Las Vegas crowd went nuts. Could an inexperienced athlete beat a credentialed former UFC champion in his second fight? Nope. Mir was too smart for him and caught Lesnar with a kneebar. Mir showed a lot of guts looking for a spot as strikes rained down on his head. Mir tapped Lesnar in 90 seconds to a stunned crowd. Was Lesnar exposed as a fraud or did he just need more time to learn? The MMA world would find out six months later.

Fabricio Werdum taps out Fedor Emelianenko June 26, 2010 - He is human after all. Fabricio Werdum tapped out Fedor Emelianenko and shocked the world at Strikeforce. This was the first loss for Fedor Emelianenko since the blood stoppage in 2000 and arguably the biggest upset in MMA history. Even more shocking is that the win came seconds into the fight via tap.

Fedor Emelianenko engaged Fabricio Werdum and hit him with a flurry of strikes. Fabricio went down and Fedor went after him. I immediately thought that this was a terrible move for Fedor. The story going into the fight was that Fabricio had the superior BJJ game and if it went to the ground, Fedor could be in trouble. It went to the ground and Fedor was in trouble. Fabricio immediately caught him in a triangle, trapped Fedor, and tapped the Last Emperor for the first loss of his career (unless you count the blood stoppage in 2000).

The loss was the first of Fedor’s career and supports many critics who thought that Fedor was overrated the last few years. While Fedor was routinely ranked as the best MMA fighter in the sport, critics cited Fedor’s lack of competition as reason why he shouldn’t be ranked highly. It has been almost five years since Fedor has fought quality competition and it looks like there was something to it.

Antonio Silva defeats Fedor Emelianenko via TKO February 13, 2011 - As dramatic as Fedor’s last loss to Fabricio Werdum was, this one was huge. Fedor was a 5-1 favorite coming into the fight on most books. Silva vs. Fedor was thought by most as an easy first round fight for Fedor. Most MMA fans were already talking Overeem vs. Fedor in the semi finals way before the bell even rang on this one. This was a fight that Fedor had to win.

Fedor looked great early on in the fight. Fedor came out swinging while Silva looked scared at times to engage. Silva started countering and nailed Fedor with a beautiful jab which backed up the Last Emperor. It appeared to me that it was at this moment that Silva started to gain confidence and get aggressive. Fedor continued to swing for the fences yet at the same time leave himself wide open for counters.

Round 2 was a different story and one of the most dramatic rounds I have seen since Anderson Silva vs. Chael Sonnen. Big Foot Silva dominated Fedor and was just beating him ferociously with strikes. In my opinion, if it wasn’t Fedor the fight would have been stopped as he looked defenseless at one point with Silva just dropping strikes from the mount. Silva clamped on an arm-head choke at one point and it looked like it was over. Somehow Fedor escaped and the crowd went crazy.

To me, it looked like Silva had punched himself out at this point. Silva just sat on top of Fedor for the remainder of the round, went for a kneebar, but was reversed. As the round ended I was fairly confident that Silva had blown himself up and Round 3 was going to be a much different story. Unfortunately there was no Round 3.

It was a real shame as this fight was turning into a classic. Fedor Emilenanko was dominated and on the brink of submission several times yet ended the round in a somewhat dominant position and looked ready for war. Knowing he needed a knockout to win, I think it would have been an electrifying third round and the conclusion of a classic either way. Yet make no mistake, it should have been stopped as Fedor’s eye was closed shut.

Pete Williams knocks out Mark Coleman May 15, 1998 - Mark Coleman was a wrecking machine during this time period. He just came off his first career loss to Maurice Smith, but Pete Williams was not Maurice Smith. Coleman took a year off and was thought to be coming back with a vengeance. Coleman was a heavy favorite in this fight. Williams was a replacement for Randy Couture who was injured training for the fight.

Coleman was strong, a great wrestler, decent striker, but he was huge…too huge for a long grueling fight with an MMA fighter. Williams capitalized on Coleman’s fatigue after about ten minutes and just pounded away at a defenseless former champion. Williams took advantage of his immobile target by nailing him with a kick to the face that dropped the big man in his spot. Williams’ win is still regarded as one of the biggest upsets in MMA history.

Randy Couture defeats Tim Sylvia for the UFC heavyweight title March 3, 2007 - When I wrote my blog about Couture retiring I referred to this fight as overrated. I still think some people look back at this fight as more monumental than it really was to the overall history of the UFC. However in terms of Randy Couture, it was certainly one of the biggest nights of his career and arguably the most memorable.

The fight is one of those fights that you will never forget if you watched it live. At 44 years of age, Couture came in as an underdog, although not as big as history would like you to believe. Couture was in retirement and coming off of knockout losses in his last two of three fights. He had not even fought at heavyweight for five years. The champion Tim Sylvia had 12 years, 7 inches, and about 100 pounds on Couture so the visual was quite an intimidating picture.

Couture dominated Sylvia in the fight and took down the big man like he was James Toney. Couture rocked Sylvia with a punch early and the place just went wild. The crowd went into an absolute frenzy with every takedown and Couture just continued to school Sylvia for five rounds. As a fight it was fairly one-sided although the crowd reactions made this a very exciting fight. It was a huge win and a tremendous comeback for a guy that was ready to ride off into retirement a few months earlier.

Frankie Edgar defeats BJ Penn April 10, 2010 - Frankie Edgar shocked the world and handed BJ Penn his first loss in the division since 2002, becoming the UFC lightweight champion. To some this was an upset, to others there was nothing surprising about the performance of Frankie Edgar.

BJ Penn walked into UFC 112 as a -700 favorite on the Vegas sports books going into his match against Frankie Edgar. In my UFC 112 preview, I wrote that I felt that the match was much closer than the betting odds indicated. While I didn’t expect Edgar to win the match, I knew it was going to be anything but an easy night for BJ Penn.

Frankie Edgar had a brilliant game plan. Edgar stuck and moved for five rounds with constant head movement which confused the champion for 30 minutes. BJ Penn was never able to corner Edgar and impose his will with strikes or ground and pound. Edgar never stopped moving and confused Penn with movements, strikes, and takedown attempts for all five rounds. Penn was obviously frustrated going into the championship rounds.

I don’t think there is any question that Ray Mercer knocking out Tim Sylvia in 9 seconds is the biggest MMA upset of all-time. Yet, it was not the only big upset in MMA history. Mercer’s win inspired me to look back at some of the most exciting upsets in Mixed-Martial Arts.

My first exposure to MMA was the hybrid pro wrestling/MMA company UWF. I loved the quick kicks and fast wrestling. That said, my interest in MMA goes back about 20 years. Rather than go through 20 years of MMA, I figured I’d just take a look at strictly upsets that ended in knockouts or TKO over the last few years.

Keith Jardine defeating Chuck Liddell September 22, 2007 - Keith Jardine just came off a knockout loss to Houston Alexander. After being knocked out in less than a minute, the Dean of Mean looked like easy pickings for the Iceman who had never suffered back to back losses in his career.

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This was supposed to be an easy fight for Liddell before getting a title shot. Liddell was dominated from the opening bell. This was the first time Liddell had gone the distance in five years. Jardine just picked him apart for three dominating rounds. Jardine got the win via a split decision and hasn’t done much since.

Gabriel Gonzaga knocks out Mirko Cro Cop April 21, 2007 - This was an undercard fight at UFC 70. At the time, Cro Cop had just come over from PRIDE FC where he was one of the most dominant heavyweights in the world. Cro Cop was signed with the intention of a big money match with UFC heavyweight champion Randy Couture.

This was Cro Cop’s second fight in UFC. I think the reason Brock Lesnar got a title shot in his third UFC fight was because of this upset right here. On paper, this was supposed to be an easy setup for Cro Cop. However, most people forget that Gonzaga was 3-0 at the time and would have been in line for Couture if not for Cro Cop’s signing.

Cro Cop nailed Gonzaga with a roundhouse kick early. It looked like it was over. However, Gonzaga responded with a rare Cro Cop takedown. Gonzaga surprisingly dominated Cro Cop on the ground. The finish was predictable, roundhouse kick to the head for a brutal knockout. The only difference was it was Gonzaga delivering the fatal blow to the most dangerous kicker in MMA. Cro Cop hasn’t been the same since.

Matt Serra knocks out Georges St-Pierre April 7, 2007 - UFC 69 was headlined by St-Pierre’s first defense of the UFC welterweight title. St-Pierre would be defending against Matt Serra. Serra earned the shot by winning The Ultimate Fighter. Serra was a tremendous underdog considering the fact that he barely won his last match and St. Pierre just destroyed Matt Hughes.

I remember how much I hated the fact that Serra was getting the fight. I hated Serra on The Ultimate Fighter. He was a big mouth who hadn’t done anything. Even his final match went to a controversial decision. I had no interest in seeing such a lopsided match.

This is why nothing is ever a given in UFC. St-Pierre likely felt as I and others did. He took Serra lightly. St. Pierre looked like he was toying with Serra. Serra caught him with a punch that rocked him. Serra seized the moment, mounted St-Pierre, and unleashed a barrage of punches. Serra got the win and the UFC welterweight title. Over four years later this is arguably remembered as the biggest upset in UFC history.

St-Pierre subsequently destroyed Serra in their rematch one-year later.

Seth Petruzzelli knocks out Kimbo Slice October 4, 2008 - I hesitated putting this one on the list. However, due to Kimbo’s hype it at the time this has to be considered one of the biggest upsets in MMA history, in addition to airing on CBS. Petruzzelli was a very last minute replacement for Ken Shamrock who got cut warming up for the fight.

I hesitated because on paper, this is exactly the result that should have happened. Kimbo was a product of a hype machine coming off of his fights on You Tube. Elite made him their star attraction. Kimbo rolled through his first fights, yet had a lot of trouble in his previous fight with James Thompson.

There is still a lot of mystery to this fight. Petruzelli at one point claimed he was paid extra not to take Kimbo down. Regardless, Petruzelli was an experienced MMA fighter. Petruzelli was 9-4 going into the fight, including a win over Dan Severn in 2004. If it wasn’t for the Kimbo-hype, Petruzelli would have been an easy favorite going into the fight.

The fight was over in 0:14 seconds. A right hand by Petruzelli put the star of Elite XC on the ground for the knockout. Not only did Petruzelli knock out Kimbo Slice, but he knocked out Elite XC. After word got out that Petruzelli may have been paid not to take Kimbo down, Elite’s world came crashing down faster than Kimbo Slice.

UFC president Dana White said this after the fight. “What has the guy done to deserve to be in the UFC? Nothing. I don’t consider him a real athlete or anything. He won’t win The Ultimate Fighter. The offer is out there if he wants to take it and he won’t win it. I might put a heavyweight show together just for him.”

Kimbo Slice entered the UFC in 2010 as a contestant on The Ultimate Fighter – The Heavyweights. He was eliminated in the first round of the tournament.

Dan Henderson knocks out Wanderlei Silva February 24, 2007 – This was the main-event at PRIDE FC’s second and last United States show. PRIDE FC 33: The Second Coming featured two of the biggest upsets in MMA history. Earlier that night Nick Diaz beat Takanori Gori.

This was a rematch between Henderson and Silva. Silva defeated Henderson in their first match. What you need to keep in mind is how great of a fighter Silva was at this time. Silva was one of the fiercest fighters on the planet. Silva came into the fight with 21 knockout wins.

Henderson was known as a great fighter, but too small to beat a great light heavyweight. Even with Henderson’s credentials, nobody ever saw him as a dangerous knockout artist. This was a great match on paper which was expected to end in a knockout for Silva.

It should be noted that Wanderlei was coming off a knockout loss to Mirko Cro Cop. However, most MMA fans chalked it up to the weight difference and the fact that Cro Cop was best of the fighters in the world. This was not going to be easy, yet Wanderlei was expected to easily handle Henderson.

Henderson had two knockout wins in the past six-years leading up to the fight. Henderson had made statements before the fight indicating that he’d be looking for the knockout. Henderson dominated Silva with knees and ground and pound in Round 1

Silva came out in the second round and tried to turn it into a slugfest. Silva pressed with kicks and punches, yet Henderson continued to counter. Henderson set up a spinning back fist beautifully which rocked Silva. Henderson followed up with a combination of strikes that knocked out the PRIDE FC middleweight champion for the win.

Ray Mercer knocks out Tim Sylvia June 13, 2009 - I don’t think an upset can get much bigger than a former UFC heavyweight champion getting knocked out by a 48-year-old former boxing heavyweight champion in under 10 seconds. That is what happened at Adrenaline III: Bragging Rights when Tim Sylvia took on Ray Mercer.

It should be noted that there were a lot of legal issues going into the fight. It was originally promoted as a boxing event. The event was forced to change the fight to an MMA match. Keep in mind that after changing this to an MMA match, one writer commented, “in a mixed martial arts bout, this could be the biggest mismatch since Hong-Man Choi vs. Jose Canseco.” – MMANews.com Ouch!

Randy Couture’s win doesn’t seem all that impressive now does it?

Chad Griggs defeats Bobby Lashley via TKO August 10, 2010 - The funny thing about MMA mismatches is that they don’t always go as planned. Bobby Lashley’s MMA career came to a halt in Houston after picking one mismatch too many. Chad Griggs never got the memo and handed Bobby Lashley his first MMA loss at Strikeforce: Houston.

After the announcement of Bobby Lashley vs. Chad Griggs, I let loose on a scathing blog here on the website. Bobby Lashley hasn’t fought a quality opponent in his entire two and a half year MMA career. After a few interviews where he talked about wanting to fight competition, specifically Brock Lesnar and some guy named Fedor, Lashley signed to fight Chad Griggs. Griggs had not fought since the spring of 2009 and didn’t even have a picture on his own Wikipedia page. Here we go again with the Bobby Lashley circus.

Well something happened at Strikeforce: Houston. Chad Griggs fought back. Unlike other Lashley opponents who mysteriously all froze when taken down, Griggs continued to fight. Lashley dominated the early portion of the fight but seemed to tire quickly. Griggs never went away, caught a tired Lashley and the fight was stopped at the end of the second round. The bloom was off the rose and Bobby Lashley was officially exposed as an MMA fraud.

Bobby Lashley has only fought once since, a controversial decision over John Ott that highlighted his questionable cardio while Griggs used the win to launch a successful comeback and has gone 2-0 since the fight, recently upsetting Valentijin Overeem in Dallas.

Kazushi Sakuraba defeats Royce Gracie May 1, 2000 - At the time this was considered the biggest upset in MMA history. Royce Gracie was a legend and left the UFC with the “Gracie Myth” still intact. This was Gracie’s second fight since leaving the UFC and he was expected to roll through Sakuraba just as he did Sakuraba’s mentor, Nobuhiko T akada a few months earlier.

Nobody expected a former pro wrestler to be the man to end Royce Gracie’s winning streak. Gracie’s streak of never losing a fight was either 13 or in the 100s if you listened to the hype. That is why the fans went nuts when Gracie was caught in knee bars early in the fight and it appeared he was in big trouble as the fight progressed.

This classic fight came to an end after 90 minutes of brutality. Gracie was just getting brutalized with leg kicks, but wouldn’t quit. Neither man looked like they were any closer to ending the fight than they were 90 minutes prior. Gracie could no longer stand up after suffering a broken femur and his brother threw in the towel. Sakuraba won the fight and became an instant legend in Japan.

BJ Penn submits Matt Hughes January 31, 2004 - While Penn would later go on and become something of a legend, Matt Hughes was the legend at this time. Hughes had run through all of the competition at welterweight in the UFC and was considered unbeatable. That was until he fought BJ Penn.

BJ Penn was no slouch coming into the fight. Penn had only suffered one loss in his MMA career, but unfortunately came up short in a draw against UFC lightweight champion Caol Uno. Due to the lack of competition for Hughes at welterweight, Penn decided to move up in weight and debut in the new weight class against the champ.

Hughes was extremely confident coming into the fight. “After that first round, he’ll walk back to his corner, and he’ll know he made a mistake…I will break him in the first round“. Unfortunately he never had that chance because the fight ended in the first round. After a battle for position on the ground, Penn got Hughes’ back and choked out the champ for the win and the welterweight UFC title.

Honorable Mention: Forrest Griffin defeats Rampage Jackson for the UFC light heavyweight title July 5, 2008 - Rampage Jackson was cocky, confident, and extremely arrogant coming into this fight. Not much has changed right? The two fighters first opposed each other on The Ultimate Fighter which saw Griffin’s team dominate.

Jackson came into the fight off of back to back wins over Chuck Liddell and Dan Henderson. Rampage looked unstoppable. Griffin on the other hand only had one big win on his record, a third round upset over Shogun Rua almost a year earlier. It was a nice story but nobody expected this kind of ending.

Griffin just dominated Jackson for five full rounds, obliterating him with leg kick after leg kick. Jackson had no answer for the kicks, nor did he do much to protect himself. Jackson appeared to only have one thing in mind which was to knock Griffin out. However, the leg kicks kept Jackson at a distance and he never had the opportunity to engage. Griffin won a five round decision over the champion and the loss sent Jackson over the edge, almost ending his MMA career.

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