25. Randy Couture Def. Vitor Belfort Via First-Round TKO at UFC 15
Vitor Belfort was being called by some the future Michael Jordan of MMA. He had disposed of his first three UFC opponents in a combined time of less than three minutes, and most figured him to run through Couture with the same ferocity.
In the opening minutes, Belfort was pure confidence, power, and speed, but after Couture weathered the early storm of Belfort, it was a different fight. Couture used a smart game plan of circling away from the power of Vitor, and waiting for Vitor to over-commit to one of his punches so Randy could bring him to the ground.
Vitor's punches began to lose their sting and Couture was surprisingly landing plenty of his own hard shots on the feet. After about eight minutes, Couture dropped Belfort to the ground and finished him with punches and knees against the cage.
This was the first upset in a career full of them for Couture.
24. Junior Dos Santos Def. Fabricio Werdum Via First-Round KO at UFC 90
In 2008, Fabricio Werdum was widely considered the top contender for the heavyweight title in the UFC. Surprisingly, Werdum was scheduled to face unknown Junior Dos Santos who was making his debut, while newcomer Brock Lesnar was given a shot at the title.
Coming into the bout, Werdum was more out of shape than had been seen in previous appearances. Many attributed this to lacking any real knowledge of his opponent, and frustration at not getting to fight for the title like many felt he deserved.
Just over a minute into the first round, Dos Santos came rushing forward with a right uppercut that Werdum bent right into. Werdum crashed to the floor and Dos Santos landed a couple more shots for good measure.
Dos Santos has proven himself to be a top contender at heavyweight, but in his debut, nobody was expecting that.
23. Kazuyuki Fujita Def. Mark Kerr Via Unanimous Decision at Pride GP 2000
When Mark Kerr entered the Pride Grand Prix 2000, he was considered by many to be the best MMA fighter in the world. Kerr considered himself an improved version of Mark Coleman because he was more well-rounded and had better cardio. Kerr had looked unbeatable in the UFC and in Pride, and was now taking his skills to Japan for the biggest tournament at that time.
In the first round, Kerr beat Enson Inoue and earned himself a spot in the next round against Kazuyuki Fujita. Fujita showed his toughness and strength in outlasting Kerr and winning a unanimous decision over a surprisingly inactive Kerr.
It was the first legitimate loss of Kerr's career, and would set off his downfall in and out of the ring. You can see more on Kerr's descent and this fight in the documentary “The Smashing Machine.”
22. Frank Mir Def. Antonio Rodrigo Nogueira Via Second-Round TKO at UFC 92
Though Frank Mir was coming off of a huge win over Brock Lesnar, however controversial, there were very few who gave him a chance against Nogueira. It was the general consensus that everything Mir could do, Nogueira did better.
This was before we had got a chance to see Mir's improved striking, and before we realized that Nogueira's best days were far behind him.
From the start of the fight, Mir out-boxed the legend with hard punches. Never had Nogueira been stopped before, but Mir was determined and it was his time. In the second round, Mir dropped Nogueira for the second time and finished him with punches on the ground. It was the highlight of Mir's career.
21. Mike Brown Def. Uriah Faber Via First-Round TKO at WEC 36
Fans had gotten used to seeing WEC featherweight champ Uriah Faber dominate a new challenger every few months, and Mike Brown was expected to be another.
Brown was certainly more accomplished than Faber's previous foes, but the average American fan had barely heard of him.
In the first round, Brown was focused while Faber was clearly over-confident. Midway through the round, Faber had his back to Brown and blindly spun around to throw an elbow. Brown saw it coming and countered with a devastating right hand that put Faber on his back. The fight was over instantly, and Brown was the new champ.
20. Maurice Smith Def. Mark Coleman Via Unanimous Decision at UFC 14
Mark Coleman's first defense of the UFC heavyweight title was the epitome of what MMA used to be, one discipline pitted against another.
Coleman was considered the best wrestler in MMA and Maurice Smith likely the best striker. At the time, however, striking seemed to be the least successful of all styles and most figured Coleman would take him down early and pound him out.
At the beginning, that's exactly how it was. Coleman took him down and pounded on him with a furious pace. What nobody had counted on was that Smith had developed a very intelligent guard and was able to survive the initial onslaught.
Midway through the fight, Coleman was noticeably gassed and Smith began to take advantage. For the final minutes of the fight, Coleman was unable to keep his hands up and took a barrage of hard pinpoint shots from Smith.
To his credit, Coleman refused to quit and made it to the final bell. The judges declared Smith the new champion, and Coleman was never able to defend his title.
19. Randy Couture Def. Chuck Liddell Via Third-Round TKO at UFC 43
Though Couture had just lost two in a row at heavyweight, he was given the chance to fight for a newly created interim UFC title at light heavyweight against Chuck Liddell. Basically, they wanted to give Chuck a belt and needed a credible name for him to beat for it.
Randy was by no means going along with those plans, as he showed in the fight. In the first round, Couture shocked everyone by out-boxing the heavily favored striker. Randy mixed take-downs and boxing together perfectly and after controlling the entire fight, stopped Liddell in the third round by TKO.
Couture went on to win the real title from Tito Ortiz just a few months later in a more mild upset that did not make the list.
18. Houston Alexander Def. Keith Jardine Via First-Round KO at UFC 71
Keith Jardine was coming off a career best win over Forrest Griffin, and had hopes of getting a title shot, or at least a fight against a big name. It was obvious that he was disappointed when he was given unknown Houston Alexander at UFC 71.
Everyone assumed Houston was just a bum put in to keep Jardine busy and get him another win. Maybe that is what the UFC thought he was, but he certainly didn't fight that way.
After getting rocked by Jardine early in the first round, Alexander snapped into action and began throwing knees and uppercuts repeatedly. Jardine was rocked numerous times before one more knee landed and turned out his lights.
Alexander quickly became the talk of town, but it wouldn't last long.
17. Randy Couture Def. Tim Sylvia Via Unanimous Decision at UFC 68
In another undeserved shot at a UFC championship, recent Chuck Liddell knockout victim and retiree Randy Couture was given the opportunity to fight for the heavyweight title against Tim Sylvia at UFC 68.
There were many observers that feared for Couture's health and did not want to see him on the mat unconscious again.
Nevertheless, Couture went on to shock everyone again by rocking Sylvia in the opening seconds and controlling the entire fight for five rounds. The win made him the only three-time heavyweight champion in UFC history.
16. Jake Shields Def. Dan Henderson Via Unanimous Decision at Strikeforce: Nashville
Dan Henderson is undoubtedly a legend in MMA, but apparently the UFC didn't think he was worth his asking price, so he packed up and went to Strikeforce.
In his first bout with the promotion, Henderson was matched with their middleweight champion Jake Shields. Many ignored Shields' credentials and figured this to be an easy entry to another championship for Dan.
In the opening round, it looked just as many had expected. Henderson rocked Shields very seriously, but Shields survived the round on instincts alone. Beginning in the second, Shields found his rhythm and out-grappled Henderson for the remaining four rounds. Shields had the better conditioning and ground game.
It was a slower and much longer fight than many expected, but Shields had done what he needed to do to add one of the biggest names in the sport to his resume and keep his title.
15. Seth Petruzelli Def. Kimbo Slice Via First-Round TKO at EliteXC: Heat
There was a time when Kimbo was briefly thought to be a legitimate competitor in MMA. His aggressiveness, punching power, and massive following had him headlining EliteXC events on Showtime and CBS.
Sure, the knowledgeable fans knew this guy did not deserve the attention and hype being thrown at him, but as I've stated many times, the knowledgeable fan is a very small minority in this sport.
Still, most figured they were going to see another knockout win for the pseudo face of MMA, especially because everyone tuned in to see Kimbo take on the ancient Ken Shamrock. But when Shamrock received a cut warming up for the fight, EliteXC scrambled to find the quickest replacement available.
Light heavyweight Seth Petruzelli stepped in for Shamrock and in the opening seconds, Kimbo rushed in as expected only to be dropped by a single Petruzelli jab to the chin. Kimbo was stopped by one punch in 14 seconds and the farce was over.
14. Nick Diaz Def. Takanori Gomi Via Second-Round Submission at Pride 33
Though Gomi had lost to Marcus Aurelio the year before, he had avenged that loss and put a few more impressive victories between him and that upset. Pride had plans to make it's move in America, and Gomi was scheduled to face American Nick Diaz in Pride's second event in the states.
Diaz had been a veteran in the UFC, but took the chance to fight Gomi and signed with Pride.
After a first round that saw Gomi rock Diaz numerous times and Diaz come back with his own flurry of punches, Gomi was clearly exhausted. Every punch he threw was for the fences.
In the second round, Diaz had a monster of a gash under his eye that clearly was bothering Gomi more than Diaz himself. Gomi shot in for a take-down and Diaz immediately locked in a Gogoplata. Gomi seemed confused by what he was trapped in and was forced to tap.
It was a tremendous fight and the win put Diaz back on the MMA map. The win was later overturned to a no-contest because Diaz tested positive for marijuana.
13. Daiju Takase Def. Anderson Silva Via First-Round Submission at Pride 26
Going into Pride 26, Anderson Silva was 4-0 in Pride and was next meeting a soft touch in 4-7 Daiju Takase.
Silva was taking his time in the fight and repeatedly gave up dominant positions. Takase was motivated and never looked discouraged. Late in the first round, Takase locked in a triangle choke from the bottom and squeezed it until Silva tapped out.
It made Takase a notable name, but he was never able to capitalize off of it, going 4-6-1 to this date.
12. B.J. Penn Def. Matt Hughes Via First-Round Submission at UFC 46
After failing to win the UFC lightweight title on two occasions, B.J. Penn instead jumped up in weight to challenge welterweight champion Matt Hughes for his title. Due to a lack of competitors at 170, Penn was given an immediate shot, but few gave him a realistic chance against the bigger and stronger Hughes.
All of those thoughts went out the window when the fight began. Penn looked equal in size to Hughes and he was the one that got the top position on the ground. Moments into the fight, Penn landed a very heavy right hand on the ground, dazing Hughes and forcing him to roll over and give up his back. Penn latched on a rear-naked choke and Hughes tapped out.
Penn was now the welterweight champion and tears flowed from his face. He would never get to defend the title due to contract disagreements with the UFC.
11. Keith Jardine Def. Chuck Liddell Via Split-Decision at UFC 76
At UFC 76, Chuck Liddell was pitted against Keith Jardine in what most perceived as a main event constructed to build up a showdown between Chuck and the newly acquired Wanderlei Silva. Even though Chuck was coming off a knockout loss to Quinton Jackson, few were debating who would win the fight, but rather in what round Chuck would knockout Jardine.
In a competitive three-round war that saw both fighters knocked to the canvas, Jardine was able to squeeze out a split-decision victory. It was a massive boost to the career of Jardine, who was coming off his own upset loss to Houston Alexander.
The UFC decided to basically ignore the loss and went ahead with putting Chuck and Silva together at UFC 79.
10. Anderson Silva Def. Hayato Sakurai Via Unanimous Decision at Shooto: To The Top 7
There was a time when Hayato Sakurai was considered by many the pound for pound best fighter in the world. In 2001, he was 18-0-2 and was the Shooto middleweight champion.
In his eighth defense of the title, Sakurai met 4-1 Anderson Silva. Silva out-struck Sakurai for three rounds to win a unanimous decision and the Shooto title in just his sixth fight.
Sakurai would suffer injuries in a car accident following the fight and begin a decline in his career. Silva went on to become the UFC middleweight champion and one of the best pound for pound fighters in the world.
9. Joe Warren Def. Norifumi “Kid” Yamamoto Via Split-Decision at Dream 9
Though Yamamoto was coming off a year and a half layoff, he had long been considered one of the best 145 pound fighters in the sport—certainly the best in Japan—and nobody could have imagined him losing to a 1-0 fighter who had just won his first fight in the opening round of the Dream Featherweight Grand Prix.
Joe Warren was that inexperienced fighter, a Greco-Roman champion, and he was meeting “Kid” in the second round of the tournament.
After a competitive fight that saw Yamamoto out-striking the wrestler, but Warren scoring takedowns and staying on top for long periods of the fight, the judges declared the bout a split-decision in favor of Warren. It was his second MMA fight and he had beaten one of the best featherweights of all time.
Yamamoto has experienced mixed results since this fight, but Joe Warren has proved his worth further by winning Bellator's featherweight tournament in 2010.
8. Gabriel Gonzaga Def. Mirko Cro Cop Via First-Round KO at UFC 70
To put it simply, Cro Cop was a legend of the sport expected to come over to America and run right through the UFC heavyweight division, while Gonzaga was basically a guy nobody had heard of.
Sure, Gonzaga had three wins in the UFC, but they were all on undercards against faces the average fan couldn't pick out of a lineup.
This was to be Cro Cop's first UFC main event, and his last fight before fighting for the title against Randy Couture. The consensus was that Gonzaga was there to get beat.
Well it could not have been any different. Gonzaga caught the second kick Cro Cop threw and took him down. After a couple minutes of punishing ground and pound, the referee stood them up, seemingly a favor to Cro Cop. Seconds later, Gonzaga threw a right head-kick that dropped the Croation like a bag of bricks. Not only was Cro Cop out cold, he fell awkwardly on his own knee, bending it in an angle painful to look at.
Everyone watching was in a quiet shock, and many had immediate thoughts for Cro Cop's health. I remember just hoping he would be able to wake up.
It was the beginning of Cro Cop's decline and Gonzaga would go on to fight for the title, losing to Couture.
7. Marcus Aurelio Def. Takanori Gomi Via First-Round Submission at Pride Bushido 10
In 2005, Takanori Gomi won the Pride Lightweight Grand Prix to become the first ever Pride lightweight champion. His first fight in 2006 was scheduled as a non-title bout against Marcus Aurelio at Bushido 10.
Gomi had previously gone 10-0 in Pride and was expected to walk right through Aurelio. However, Aurelio was able to put Gomi on his back and sink in an arm-triangle in the first round. Gomi refused to tap and was choked unconscious.
It was a shocking sight to see, since Gomi had been so dominant in the years leading up to that fight. Gomi went on to win the rematch in a title fight later that year.
6. Joe Lauzon Def. Jens Pulver Via First-Round TKO at UFC 63
The UFC reinstated its lightweight division in 2006 after putting the division on hold for a couple years. At UFC 63, the only lightweight champion returned to the UFC. His first match was against young submission artists Joe Lauzon, who was a 7-1 underdog.
In the first minute of the fight, Lauzon caught Jens with a left-hook and dropped him. He finished it with punches on the ground and the ref called off the fight at 43-seconds into the first round.
The crowd was in complete shock and Pulver's career began a downward spiral. Pulver has gone 1-6 since the loss and Lauzon is now a talented rising contender in the UFC.
5. Kevin Randleman Def Mirko Cro Cop Via First-Round KO at Pride Total Elimination 2004
Mirko Cro Cop was an early favorite in Pride's heavyweight tournament in 2004. Everyone was hoping for him and Fedor Emelianenko to meet in the finals in a much anticipated clash. In the first round, Mirko was set to face UFC vet Kevin Randleman.
Randleman was coming off two losses against Quinton Jackson by knockout, and Kazushi Sakuraba by submission. Mirko had only lost once in Pride, and that was a fight he was winning against Antonio Rodrigo Nogueira before getting submitted in the second rounds.
In the opening seconds of the first round, Randleman came forward and threw a powerful left-hook that dropped Cro Cop. Immediately, Randleman pounced on his hurt opponent and knocked him out cold with punches on the ground. It was a quick and shocking defeat.
Randleman went on to face Emelianenko in the next round, creating one of the most spectacular highlights in the sport by slamming Emelianenko on his head. Emelianenko still came back to win the fight.
4. Forrest Griffin Def. Mauricio Rua Via Third-Round Submission at UFC 76
In 2007, Mauricio Rua was the No. 1 light heavyweight in the world and was making his UFC debut. Forrest Griffin was just one fight removed from his devastating first-round knockout loss at the hands of Keith Jardine, but was begging the UFC to be Rua's first opponent in the UFC.
Griffin got his wish and the two met at UFC 76. After a competitive first half of the fight, and Forrest suffering a humongous gash on his forehead from a Rua elbow, Rua became noticeably exhausted. He was having a hard time keeping his hands up and was gasping for air through his mouth.
In the third round, Griffin took over and unleashed a series of blows to a grounded Rua. With just 15 seconds left, Forrest sunk in a rear-naked choke and forced Rua to tap. Forrest ran across the ring celebrating and history was made.
Forrest parlayed that win into a title shot, which he won. Three years later, Rua would become the champion as well.
3. Rameau Theirry Sokoudjou Def. Antonio Rogerio Nogueira Via First-Round KO at Pride 33
There are some that would claim this to be the biggest upset of all time because of the insanely lopsided betting odds that had Nogueira somewhere around a -2500 favorite. It certainly could be at the top of the list, but it was a fight of little importance and anticipation, so we will save the top spots for fights that took place on a bigger stage.
Sokoudjou was a champion in judo, but had very little MMA experience with a 2-1 record, and was coming off a first-round knockout loss just a few months earlier. Nogueira was a top contender at 205, and had been in tremendous battles with the elite fighters of his division.
In the opening seconds of the fight, Sokoudjou landed a high kick, left hook combination and knocked Nogueira out cold. The fight was over in 23 seconds, leaving the crowd in shock at what it had just seen.
Nogueira has not lost a fight since, while Sokoudjou has found little success since.
2. Fabricio Werdum Def. Fedor Emelianenko Via First-Round Submission at Strikeforce: Fedor vs. Werdum
After going undefeated in a career spanning 10 years that saw him become the Rings and Pride heavyweight champion, Fedor was set to meet Brazilian jiu-jitsu ace Fabricio Werdum in a Strikeforce main event.
Emelianenko had an aura of invincibility due to his long and accomplished career without a legitimate loss. He had also dominated fighters of a similar style as Werdum and fighters that had themselves beaten Werdum. It was going to be a good win for Emelianenko, but nobody figured him to be in any danger at all.
In the opening minute, Emelianenko was swinging for the fences and Werdum fell to his back. Fedor charged in without any caution and tried to finish the fighter that he thought was hurt. Werdum was not hurt and he quickly locked Emelianenko in a triangle choke. Emelianenko struggled to get out and Werdum pulled an arm bar to boot. After about 30 seconds of being stuck in the choke, Emelianenko gave one solid tap.
It was the end of an era. The great Emelianenko had tasted defeat and MMA would be changed forever. Werdum would finally get credit for being a top heavyweight.
1. Matt Serra Def. Georges St. Pierre Via First-Round TKO at UFC 69
After winning season four of The Ultimate Fighter, Matt Serra was awarded a title shot against Georges St. Pierre. Most considered this more of a punishment than a reward, assuming Serra was in for quite a beating from the unstoppable looking champion.
St. Pierre had just won the title from Matt Hughes at UFC 65 in dominant fashion with a second-round head-kick TKO. Serra was figured to be an easy first defense for the new champ.
The two met at UFC 69, with most betting odds listing St. Pierre at around a -1000 favorite. After a few minutes of feeling each other out, Serra connected with a right hook on the ear of St. Pierre. With the champion clearly wobbled, Serra pounced on him with a series of punches, knocking him down and finishing him with strikes on the ground.
The bout lasted less than three and a half minutes. Serra was the new champion and St. Pierre would be forced to reassess his career.
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