Top Five Greatest Middleweight Fights of All Time

Top Five Greatest Middleweight Fights of All Time

May 30, 2024|

We've seen our fair share of great fights as of recently, but on paper, the UFC 302 co-main event between former Middleweight champion Sean Strickland and former Middleweight title challenger Paulo Costa seems like one we could very well add to that list. The people's main event will be a five-round treat for fans, who will expect a war this weekend in New Jersey. The winner will put themselves right at the top of the list to challenge for Dricus Du Plessis' title in the near future.

To get us ready for this Middleweight showcase, let's take a look at the top five greatest fights in the UFC Middleweight division's history.

Yoel Romero vs Paulo Costa - UFC 241

The featured bout at UFC 241 was on a lot of fans' radars, as Yoel Romero and Paulo Costa was a clash of two physically imposing and extremely dangerous fighters in the division. This fight delivered, as we saw these go right at each other for the entirety of the fight. Costa came out very aggressive, looking to put Romero away early with some heavy blows. Both men scored early knockdowns, and the fight carried to the judge's scorecards, with both men gassed but still giving everything they had. In the end, Costa won a split decision and went on to challenge for Israel Adesanya's Middleweight title.


Anderson Silva vs Michael Bisping - UFC London

Once Anderson Silva lost his title following consecutive losses to Chris Weidman and a no-contest with Nick Diaz following a failed drug test, the GOAT was looking for a way to reinsert himself back into the picture, and a showdown with Michael Bisping in his home backyard was just the way to do that. Bisping was the fan favorite in this fight against Silva, and the electricity of the crowd made it even more memorable to watch. Late into the third round, Bisping's mouthpiece was knocked out. Expecting a stoppage of the action, Bisping was distracted, leading Silva to land a flying knee that landed flush on Bisping and sent him crumbling to the canvas just as the bell rang. Silva thought that the fight was over, and he jumped onto the octagon cage to celebrate. Fortunately enough for Bisping, the round was just over, and he was given time to recover. Bisping then rallied, bloodied and with a giant mouse under his eye, to defeat the greatest of all time. Bisping's performance earned him a title shot against Luke Rockhold, and you all know how that went.

Robert Whittaker vs Yoel Romero II - UFC 225

Either fight between the rivalry of Robert Whittaker vs Yoel Romero could easily be on this list, but I decided to go with their second fight at UFC 225. In the first meeting, Whittaker won a unanimous decision and earned the interim middleweight title. The two were destined to meet again, and so they did at UFC 225 in Chicago. Unfortunately, Romero missed weight and was ineligible to win the title, but he still put on a memorable fight that is still talked about to this day. Whittaker dealt with a broken hand early in the fight but persevered and continued to fight off Romero's onslaughts. Romero put it on Whittaker in the third and fifth rounds, but it wasn't enough as Whittaker won a very close split decision, retaining the title.


Israel Adesanya vs Kelvin Gastelum - UFC 236

The UFC 236 main event was a clash between two top contenders in the Middleweight division for the interim title. Israel Adesanya was this undefeated prospect out of New Zealand who looked to have what it took to become a future champion. Gastelum was a seasoned veteran who was looking at his first opportunity at UFC gold. These two went to war and showcased true heart, grit, and determination. Both men were desperate to touch the interim title, Adesanya came with elite precision and technical striking, while Gastelum pressured forward for all 25 minutes of the fight. In the fifth and final round, Adesanya dropped an exhausted Gastelum multiple times, winning him the interim title. This fight solidified Israel as a future star and a "must-watch" fighter.

Anderson Silva vs Chael Sonnen I - UFC 117

The greatest Middleweight fight of all time is almost a no-brainer. Anderson Silva, the reigning champion and one of the greatest of all time, was in the midst of a historic and legendary run as the Middleweight champion. He had a sense of invincibility around him, nobody was able to figure him out or even come close to defeating him. Silva fought Chael Sonnen, a confident and brash wrestler at UFC 117, and many expected another dominant showing from the champion. Fortunately for us fans, we were dead wrong. Sonnen dominated Silva with his wrestling and control on the mat for four and a half rounds. Silva, down in the fight and at risk of losing his title, threw up a Hail Mary triangle armbar and submitted Chael Sonnen with just minutes left in the fight. It was shocking to see Silva get dominated like that in a fight, proving that he is human, but it was even more shocking to see him come back, face serious adversity, and remain the Middleweight champion of the world.

This weekend, we have a spectacular Middleweight clash between Sean Strickland and Paulo Costa, two fighters who know exactly how to put on exciting fights. This should be a barnburner on a spectacular card going down in Newark, New Jersey, this Saturday night.

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