5 Best UFC Fights in Madison Square Garden

The UFC made a major push to get the sport of MMA legalized by New York State legislature back in 2016. It was the last state to legalize it after a strong push by the late United States Senator John McCain to get the sport of “human cockfighting” banned. 

The UFC celebrated the sport’s legalization by bringing a historic card to the world’s most famous arena in Madison Square Garden. After the success of their first card, the UFC has made November the month to host a UFC event in The Garden and this weekend, we have that annual event with another stacked card. 

The stacking of these cards has resulted in some legendary bouts unfolding under the bright lights of New York. Let’s look back on those before we set ourselves up for more historical moments this weekend.

McGregor Becomes the Double Champ 


Randy Couture and B.J. Penn had been two-division UFC champions but never at the same time. Conor McGregor was the featherweight champion when he entered a bout against lightweight champion Eddie Alvarez at the UFC’s debut event in New York City. What would happen leading up to the event is arguably the greatest McGregor one-liner that he exchanged with Jeremy Stephens but followed that up with a historic performance. McGregor would piece up Alvarez for all intents and purposes as he made the “Underground King” look like he just crawled out of his hole. 

St. Pierre Returns for History 

A moment in UFC and MMA history that has seemingly been forgotten is the return of welterweight legend Georges St-Pierre but this time he was fighting at middleweight. He would be fighting a fellow legend in Michael Bisping.

For St-Pierre, this almost seemed as if it was a one-off event for him. Winning the middleweight title would be another notch in the already impressive belt. In the case of Bisping, it allowed him to fight one of the best of his era and possibly send him into that all-time tier in the sport’s history. While Bisping didn’t win the bout, I personally think he still earned that.

Both men took a beating and put on an all-time performance to the delight of MMA fans and those in attendance at Madison Square Garden that night. St-Pierre earned the victory with a third-round rear naked choke.

The BMF Belt is Established 

What do you get when you have a pre-fight press conference where a fighter dresses as Tony Montana, a new “division” with a new belt, and Dwayne “The Rock” Johnson? You get the event that was UFC 244.

The UFC usually just goes with interim title fights to bulk a card but that wasn’t enough on this occasion. Dana White and the UFC created the “Baddest Mother…”, well you know the saying, belt. The fight for this belt would come when Jorge Masvidal and Nate Diaz would fight in what was, on paper, the most fan-friendly matchup in UFC history. One problem is that in a fight between these two, there of course will be violence and the New York State Athletic Commission is still very new to the sport of MMA.




The bout would be entertaining for as long as it would last which would be a mere three rounds as Diaz was too cut up for the commission doctor’s liking and he would call an end to the bout. Masvidal would win the “BMF” belt with Dwayne Johnson putting it around him of course. Sadly that is the last anyone has seen of the belt since.

Gaethje and Chandler Steal the Show 

Easily the best fight in the history of the UFC in Madison Square Garden is the meeting between Justin Gaethje and Michael Chandler. Both men had wrestling backgrounds but had developed the reputation as being violent knockout artists before entering the UFC. Chandler in Bellator and Gaethje in what is now the PFL, were perfect examples of the UFC signing the best talent to create dream fights for the fans. 




To say this fight lived up to the hype would be an understatement. Both men started round one by just blasting each other with their best shots before continuing the same routine in round two. Both men looked bloody and battered entering round three and yet they still brought the same mentality. It would be many people’s fight of the year and is considered one of the best in the sport’s history, period.

Usman and Covington Settle Their Beef

At the same event that we were treated to Chandler versus Gaethje, fans also got the grudge match between then-pound-for-pound king and welterweight champion Kamaru Usman and challenger Colby Covington. Of course, these two had met previously with Usman poetically breaking Covington’s jaw after months of trash talk. In this meeting, however, the former American Top Team talent would make things much closer.

Covington and Usman knew the dangers each man presented and were cautious at times but still found ways to be aggressive. Both men were able to neutralize the others’ wrestling and we ended up having more of a kickboxing match. This favored the Nigerian Nightmare as he would earn a decision win but it also won Covington over with some fans. 

A hot mic would catch both men discussing the harsh war of words leading up to the bout that were perfect for selling the fight thus creating their own CM Punk pipebomb moment in a way.

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