With the whirlwind of events surrounding UFC 223 and the losses the card took , I started to think about all of the losses in UFC history that were huge. Whether the fight had big stakes at hand, or the fight just changed the course of a fighter’s career, I sought out to make a list of the Top 5 times a loss felt like it meant so much more.

 

No. 5. B.J. Penn vs. Nick Diaz

 

While I was tempted to pick Edgar vs. Penn for this list, that fight will have to remain an honorable mention because Diaz vs. Penn proved to be pivotal in the career in both men. It is interesting to note that since this fight, neither fighter has managed to get a win in almost 7 years.

In a Fight of the Night performance that stands the test of time, Nick Diaz brought a level of war to B.J. Penn that the Prodigy wasn’t ready for to say the least. For the first few minutes, both men showed the UFC fans how experienced they were in almost every facet of the sport. Towards the end of the first round, Diaz started to gain a level of confidence with his strikes that would change the pace of the rest of the fight.

The next 2 rounds, Diaz would wear down the smaller Penn, by pressing the Prodigy against the cage and unleashing a barrage of body shots. By the end of the second round, what started as a pretty even back and forth, turned into the Nick Diaz show, and Penn was struggling to make it bell to bell.

I think it is easy to say if Diaz was fighting a lesser fighter, they probably wouldn’t have made it the full 15 like Penn did. In the 3rd round, Nick continued his relentless assault on Penn, and would make sure to taunt Penn, in an attempt to crush the former Lightweight champion’s spirit. While Diaz would walk away with the win and a future shot at the welterweight championship, Penn’s future in the octagon would be much bleaker.

It was the fight against Diaz that started a streak of losses that the Prodigy had never seen in his career. B.J. has struggled with the notion of retirement over the years, but most UFC fans would agree that the Hall of Famer has nothing left to prove. Time will only tell if Penn ever decides to step into the octagon one more time, or hang up the gloves for good.

 

No. 4. Renan Barao vs. T.J. Dillashaw

Amongst UFC fans today, it is almost common knowledge to refer to the 2 time Bantamweight Champion T.J. Dillashaw as one of the greatest fighters in the world today. 4 Years ago, the Bantamweight landscape was a very different beast though, and no fighter ruled the division as dominantly as Renan Barao. The Bantamweight Champion at the time, Barao was riding one of the longest UFC undefeated streaks the sport had ever heard of, and many didn’t give Dillashaw much of a chance of changing that. How wrong everyone was.

In what would be one of the more memorable walk outs in UFC history, Dillashaw came to the octagon with the song that will be forever linked to him, “Can’t Stop” by the Red Hot Chili Peppers. The hit by the Chili Peppers echoed like an anthem that night, as Dillashaw put on one of the most incredible performances fans of the sport had ever witnessed.

The first few minutes of the fight felt as if we were about to witness a slaughter, as both Joe and Mike would remind us that at any moment Barao could finish Dillashaw. It didn’t take long for T.J. to show off a skill set that Barao wouldn’t even imagine keeping up with. After the first 4 minutes Dillashaw would knock Barao down and show the world that Barao’s streak was about to end.

In between the first and second round we were shown Barao sitting on a stool in his corner, and the champion was visibly shaken from the last minute of events of the first round. The bell rang, and Dillashaw picked up where he left off in the first round, picking apart Barao with unpredictable strikes and footwork. The speed and power from Dillashaw were the best they could ever be that night, as he would continue to show through the next three rounds.

It was the 5th round where Dillashaw put the topping on his already great performance, where he proceeded to go “Ultra Instinct” and finish Barao with a combination of the strikes that would undoubtedly earn T.J. the nickname “Killashaw”.  While this loss isn’t about someone’s fall from grace, it shows how the unpredictable sport of MMA can give us some of the best underdog moments we could ever wish for and how those moments can elevate a fighter to greatness.

 

No. 3. Jose Aldo vs. Max Holloway

I could easily put the fight between McGregor and Aldo on this list and not many would argue that loss was a pivotal one in UFC history that really put the Featherweight division front and center. While that fight took only 13 seconds to make history, I decided to go with Holloway vs Aldo instead, because it was a true passing of the guard from the old champion to the new champion.

With McGregor decidedly out of the division at the time these two fought, the UFC paired Jose Aldo against young Max Holloway, who was riding an impressive 10 fight win streak. The fight took place in Aldo’s native home of Brazil, and the fight would determine who would reign over the Featherweight division as the champion.

The first round saw Aldo in classic form, as he used his striking to get the better of Holloway. This fight really started the same way as a lot of Aldo’s fights do, with the opponent not really able to stop the pressure of the Brazilian. Max had an unorthodox game plan that turned out to be part of the key of beating Jose. The plan was the weather the early storm from Aldo, and once Aldo was wore out, to turn things up a bit.

That is exactly what Max did, and this was on showcase the most in the 3rd round. It didn’t take long at all for Holloway’s conditioning to show through, with his speed and pressure allowing him to get into a rhythm so Max could dictate the fight.

Once Max was “warmed up”, it only took 3 minutes into the 3rd round for him to drown Aldo in strikes in a way that no one ever has before. It was one of the most vicious championship performances of recent memory that left the entire crowd in a mix of silent heartbreak for Aldo, and booing the beginning of the “Blessed Era”.

This loss shows the transition of MMA over time. We always talk about the sport evolving and this is a shining example of one fight where you get to see that evolution take place. Max used champion mentality and strategy to capture his dreams that night, and repeated his performance against Jose Aldo just a short 6 months later, showing that the next generation of UFC elite is here to stay.

 

No. 2. Chris Weidman vs. Anderson Silva

Let’s take a trip to the past. The event is UFC 162, and it is headlined by one of the greatest fighters to ever enter the octagon on a night that many UFC fans will remember forever. Anderson “The Spider” Silva, who at the time was undefeated in the UFC, was known by many as simply the Greatest of All Time. If you were a fan at the time, it would be hard to argue that fact, because time after time Silva would showcase just what a special athlete he is.

Enter Chris Weidman. The American Underdog came to the cage that night with an undefeated streak of his own, and looked to shock the world by beating “the Spider”. On paper, Weidman had all the tools it would take to beat Anderson, but the Vegas betting odds weren’t giving him much of a chance come fight night.

The 1st round was electric as Anderson worked up the crowd and repeatedly taunted Weidman, as Silva had done to many opponents before. Switching stances and getting Weidman to engage in a dangerous chess game, Silva was all but executing his gameplan wonderfully in the first round.

“Punch a f***ing hole in his chest”, iconic words shouted from Ray Longo between rounds to Chris Weidman. Longo, who is Weidman’s longtime coach, reminded Weidman that he is more than talented enough to beat Anderson.

One of the more shocking defeats in UFC history came just a short few minutes later. As the 2nd round started, Silva went back to the mental games of taunting the younger Weidman. While Silva’s striking was crisp, his careless taunting would lead to one of the more upsetting moments in his career. Silva, who was more concerned about dance moves it would seem, mocked Weidman and ate a devastating left hook for his trouble. Weidman knocked Silva out cold and the crowd erupted. That night not only crowned a new Middleweight Champion, but it also marked the end of the dominant Silva we had always known.

The rematch between these two more than deserves mention on this list, if nothing more than for the crushing second loss and injury the former champion suffered. Anderson, who was focused on reclaiming the championship he had held for so long, went toe to toe with Weidman once again at UFC 168.

As “Ain’t No Sunshine” played throughout the arena, many felt how strange it was to hear that song first, as the first song always indicates the challenger. No song is more fitting of a fighter though than Tom Petty’s “I Won’t Back Down” is for Chris Weidman. Coming off a history making performance in the first fight, Weidman was looking to capture lightning in a bottle once again.

The beginning of the fight was noticeably different, with Weidman looking far more composed than he did in the first fight. Early in the round he injured Silva, and Weidman was closing to finishing Silva for the second time in his career. Weidman was finally able to showcase the outstanding wrestling that many were expecting in their first fight, and Silva managed to survive to the end of the first round.

It was the second round that had one of the more shocking injuries we have witnessed in the sport. In the first fight between these two, Silva had a fair amount of success with his leg kicks against Weidman. In preparation for their second bout, Weidman worked on checking those kicks with his knee, a strategy that would prove to benefit him the second time around. It didn’t take long for Silva to start throwing his leg kicks in the 2nd round, but almost as quickly as he started throwing them, Silva collapsed to the floor in agony after a checked kick from Weidman.

The fight was immediately stopped with Chris awarded the victory, however, the celebration in the arena quickly turned to gasps as we were shown the replay of what had happened to Anderson. In slow motion, the cameras replayed the moment where Silva’s shin hit Weidman’s knee. Silva’s shin shattered upon impact and proceeded to wrap around Weidman’s leg in a scene tough for viewers to watch.

A loss in itself is tough to come back from, but if you add on an injury it’s easy to see why Silva has never really looked quite the same after the Weidman fights. The story between the two may have ended that night, as they haven’t been paired up again since, but there is no doubt that both men will go down in the history books as being some of the best to ever enter the octagon.

 

No.1. Nate Diaz vs. Conor McGregor

“Nate Diaz, you just shook up the world, how’s that feel?” were the first words Joe Rogan said to Nate Diaz after his dominant victory over Conor McGregor. The native from Stockton replied in a way that only a Diaz brother would.

“Ay, I’m not surprised mother f***ers”.

That night, Diaz not only gave McGregor his only loss in the octagon, he became a superstar in the UFC. To say Diaz’s stock rose after that fight is definitely an understatement, considering he not only beat one of the UFC’s top stars, but he did so on two weeks notice to prepare for the bout.

In a fight that went on to win submission of the year, Diaz and McGregor proved that they are not only some of the sport’s more polarizing figures, but that they are some of the best strikers too.

McGregor took the fight to Diaz early, and worked on closing the distance with his unorthodox strikes. Conor was definitely more than effective, catching Nate with shots that caused a bit of damage early. The round came to a close with McGregor imposing his will on Diaz, but it wouldn’t last for long.

Before the fight, Diaz was a huge advocate against the UFC’s preferential treatment of McGregor, and would voice his displeasure at any chance possible. Accusing Conor of “taking everything he worked for”, Diaz had a chance to back up his complaints in the octagon and this was no more apparent than in the second round. Diaz started to turn the pressure up in a way that only a Diaz can, and began to eat McGregor’s shots and respond with clean counters. It wasn’t long before multiple shots to the chin put Conor in deep water against one of the best boxers in the sport.

In desperation, McGregor dove at Diaz for a takedown that set off the chain of events that would lead to Diaz submitting McGregor in the middle of the octagon. The two men scrambled on the ground for a moment, with Nate Diaz quickly gaining dominant position as he took McGregor’s back and locked in a Rear Naked Choke. Once the choke was sunk in, it didn’t take long for McGregor to tap and the whole arena to erupt from the sheer magnitude of what just happened.

This loss was hard to top for a few reasons. While no one likes to lose, McGregor didn’t really take much of a set back from the loss, and McGregor was incredibly humble in defeat to the surprise of most people who have followed the brash Irishman. The fight actually brought Nate up to superstar level, and created a rivalry that both men arguably needed. This fight, like others on the list, lead to a rematch, but unlike Weidman/Silva or Holloway/Aldo, McGregor was able to redeem his performance and score a win over Diaz. Now, a few years and a huge Mayweather fight removed, McGregor vs Diaz 3 is still one of the most highly anticipated rematches than fans want to see.

 

That concludes my list of the Top 5 losses in UFC history. Is there a fight that you thought should’ve made the list? Comment below and let me know.  Feel free to follow me on instagram or twitter @StephenAtKwinn and stay subscribed for more Top 5 lists and UFC coverage.