The moment James "Buster" Douglas landed the knockout blow to finish Mike Tyson in their heavyweight championship bout in 1990, fight fans from around the world witnessed what is still considered one of the greatest upsets in combat sports history.
At that time, the sport of mixed martial arts wasn't even a real entity yet. It wasn't until three years later that a group of promoters got together and created the Ultimate Fighting Championship—billed at the time as a "no rules" competition to pit every fighting style against one another until only one man was left standing.
Fast forward 13 years later and the UFC was thriving as a growing sports product on pay-per-view and free television after the landmark launch of The Ultimate Fighter reality show. Through three seasons, the UFC had capitalized on a new crop of young fighters to bolster their roster of talent with tons of future stars being born during those years.
It was during the fourth season that the UFC gambled on a different version of the show.
In past years, the show was promoted around two UFC veterans who served as coaches and a list of up-and-coming hopefuls who wanted to earn their way to the Octagon via The Ultimate Fighter. In the fourth installment, however, the UFC decided to give some old dogs the chance to prove they could learn some new tricks.
The Ultimate Fighter: The Comeback featured 16 former UFC fighters all hoping to land a second shot in the promotion after having been cut in their previous stints.
It was a mixed bag of fighters with experience that reached all the way back to UFC 16 (in the case of Mikey Burnett) and all 16 of the competitors had something to prove after making it to the big show before being sent back down to the minors.
One of those cast members was Matt Serra, who had fought in the UFC a total of eight times previously, amassing a 4-4 record overall with almost all of those fights taking place in the lightweight division.
It was at UFC 53 in 2005 when Serra bumped up to welterweight for the first time, but lost to then-rising star Karo Parisyan before exiting the promotion until later that year when The Ultimate Fighter Season 4 started production.
The contestants on the show also had one extra incentive laid at their feet in addition to enticement of earning their way back to the UFC Octagon. The two winners of the show (one at welterweight and one at middleweight) would earn title shots against the champions in their respective divisions when the season came to a close.
It was the first and only time that stipulation was added to the reality show's stakes, and it made for an even bigger prize once it was all said and done.
The show that season featured a cast of characters with potentially more alpha-male types than in any other version of The Ultimate Fighter. In the house, there were 16 fighters who all had UFC experience, and none of them wanted to give an inch either in training or during the fights.
As the show wore on, however, many of the fighters started to turn to Serra for his advice and coaching, having been a longtime jiu-jitsu instructor under famed coach Renzo Gracie.
Serra's voice was not only the loudest and most recognizable (there's just something about that thick New York accent he carries), but he was also clearly the most knowledgeable one whom other fighters could turn to without thinking he was playing them for a fool just hoping to make it to the finals himself.
It turns out once the show was over, Serra not only served as the de facto coach, but he was the most successful fighter as well, and it was in The Ultimate Fighter 4 finale where he met former housemate Chris Lytle with a chance to win the reality show crown as well as a UFC welterweight title shot.
The fight between Serra and Lytle wasn't one that will be remembered for much unfortunately. It was a ton of clinching against the cage as each fighter tried to rally for position, but when it was over, the judges gave the nod to Serra by split decision.
It wasn't the kind of performance Serra hoped to give—especially knowing that this one fight would then set the stage for his showdown with the UFC welterweight champion.
One week after Serra's sluggish win over Lytle earned him the title shot, 25-year old Georges St-Pierre captured the UFC welterweight title with a knockout win over legendary champion Matt Hughes. St-Pierre was the UFC's new golden boy—a true hybrid fighter who marked the next generation of mixed martial artists competing in the Octagon.
St-Pierre looked unstoppable through his run of victories up to the moment when he slammed his shinbone into Hughes' face to knock the former champion to the mat before battering him with punches to win the fight and claim the welterweight title for the first time.
Despite the fact that it was St-Pierre's first UFC title, he was hailed as the next great champion that the promotion would build around for the next decade. He had already racked up wins over several top contenders including former champion B.J. Penn, Sean Sherk and Frank Trigg.
His first title defense would then come against Serra almost exactly six months later, and St-Pierre was declared as a huge favorite before the night began. The Canadian was a whopping -1100 favorite at one point before the fight with Serra took place. Most looked at the bout as a formality for the champion before he started his climb into the deepest part of the welterweight division.
No one believed Serra could pull off the impossible and beat St-Pierre.
Heading into the fight, Serra knew he was being considered an underdog—maybe the biggest underdog in MMA history. Serra explained his situation when speaking to MMAWeekly Radio in 2006, just a week out from the fight:
It helps motivate me for sure and the fact that I'm such a huge underdog, hey man that's no sweat to me. If anything, that's worse for him. Every round that I'm in there with him, people are thinking I shouldn't be in there with him. He should have took me out two rounds ago or one round ago.
The long odds didn't seem to rattle Serra, but he knew that there was no playing around with an athlete the caliber of St-Pierre. His strategy was simple—get in his face and never let up on the pressure until the fight was over.
"I'm just going to try to force him to make a mistake," Serra said later in the same interview. "I'll be in his face and the one thing I can tell you is I'll be game."
When asked for a prediction for the fight, Serra didn't try to inflate his own ego by saying he'd knock out St-Pierre or submit him on the ground. He sounded just confident enough that he'd stick around and make it a good fight.
To give his final call for how the fight would go down, Serra called on some wise words by his coach and mentor Renzo Gracie to draw on for inspiration as he stepped into the biggest moment of his fighting career.
I hate to quote Renzo on this but I'm going to go forward and see what happens. That's my favorite line from Renzo. I trained hard, I know it's going to be war and that's what I've prepared for. I've been the hammer in some fights and I've been the nail.
Everyday after that fight I can look at myself in the mirror whether I was victorious or not. I don't get swept up into the whole hype of things. I'm going to stay in the moment, I'm going to go out there and try to fight my best. Hopefully we do all right.
UFC 69 took place on April 7, 2007, at the Toyota Center in Houston, Texas. With over 15,000 fans in attendance, St-Pierre stood tall in the Octagon as the main event began. When referee "Big" John McCarthy pulled him and Serra to the center, it appeared as if the two fighters should be in different weight classes, not sharing the same cage.
Before the first round kicked off, UFC lead commentator Mike Goldberg said, "will tonight be the defining moment of Matt Serra's career?". Little did he know he was about to become the greatest prognosticator in all of MMA.
As the fight started, St-Pierre was a physical specimen who towered over the much shorter and stockier Serra. Former UFC heavyweight and light heavyweight champion Randy Couture, who was working the commentary booth that night, mentioned early on that Serra had to get on the inside of St-Pierre's reach or he was going to have a long night of punishment doled out to him as the fight wore on.
"Georges has six inches of reach, he's a very dynamic striker with his feet and his hands," Couture commented. "He'll use that long jab and keep Matt out at bay all day long and pick him apart. He's going to eat them all night if he doesn't get past that range."
St-Pierre's attacks were quick as he launched kick after kick aiming at Serra's head, looking for his second knockout in a row after finishing Hughes with the same kind of strike. Serra wasn't going to be intimidated, however, and kept coming back with body shots any time he could get inside on the Canadian.
Almost like he knew he could get the knockout at any time, St-Pierre toyed with Serra by continuously throwing kicks while bouncing up and down on his feet.
With just over two minutes left to go in the first round, one punch changed everything.
Serra connected with a looping right hand that clipped St-Pierre just behind the ear, and as he wobbled backward, struggling to catch his balance, it was clear that the shot landed better than most expected. Serra swarmed with punches, and at one point, St-Pierre fell flat onto his hands and knees as UFC color commentator Joe Rogan shouted "he's hurt!".
St-Pierre tried valiantly to get his legs back under him, but Serra was unrelenting with his attacks and again tagged the champion with a quick left-right combination that dropped him to his knees. With his head rattled and air running out, St-Pierre tried to grab a hold of one of Serra's legs, but couldn't get any traction and tried to bounce back to his feet.
It was then that Serra connected with one more big right hand that sent St-Pierre crashing butt first to the mat.
"He's hurt bad!" Rogan screamed over and over again as Serra rained down shots from above.
Serra didn't let up until St-Pierre rolled to his side and signaled for the referee to step in and stop the fight. McCarthy finally stopped the offensive onslaught, and as Serra jumped up in celebration and did a one-handed cartwheel, Rogan captured the moment perfectly with one word.
"Unbelievable," Rogan shouted. "Unbelievable!"
The official stoppage came at 3:25 in the first round, and just like that, Matt Serra pulled off the improbable, the unexpected and as Rogan put it best—the unbelievable.
Smiling from ear to ear when Rogan approached him with the microphone after being announced as the new UFC welterweight champion, Serra didn't get too caught up in the moment and even managed to throw in a little humor after being portrayed for weeks as the underdog who had about a snowball's chance in hell of beating St-Pierre.
"Joe, I'm really, really hungry," Serra said. "I was wondering if you and Dana had some humble pie in the back?"
Now seven years after the historic night versus St-Pierre, Matt Serra walked away from the sport and retired last week following an 11-plus year fight career.
Serra fell to defeat in the rematch with St-Pierre a year later, but just like how Douglas lost in his next fight after snatching the title from Tyson, it's not a moment that stands the test of time like how the upset will live forever.
Serra retired with an overall record of 11-7 and a career built on great fights and a personality that may never be matched again by any fighter who competes in the Octagon.
Many fighters will amass a similar record and maybe even win a title along the way, but it's hard to say if they'll be remembered five or 10 years from now. There's no doubt, however, that on that April night in Houston, Texas, Serra secured his legacy forever when he shocked the world with the biggest upset in mixed martial arts history.
Damon Martin is a Featured Columnist for Bleacher Report.