UFC 322 - Remembering the First Six Madison Square Garden Main Events Ahead of November's JDM-Makhachev Showdown

Madison Square Garden, the site of November’s UFC 322 - Source: Unsplash

After months of speculation, on August 29th, the UFC finally confirmed the welterweight title clash that we all expected. Newly minted champion Jack Della Maddalena will defend the 170-pound title against former lightweight king Islam Makhachev in a blockbuster showdown at UFC 322 inside Madison Square Garden.

Makhachev’s Welterweight Title Tilt

Fans had been hopeful of a similarly mouthwatering clash between Makhachev and Ilia Topuria after the latter vacated his featherweight gold to move up to 155 pounds. However, when the former followed in his adversary's footsteps by going up a division, it became clear that JDM vs Makhachev was the direction that UFC brass would head in.

Online UFC odds providers consider the Dagestani former lightweight champion a narrow favorite heading into the showdown. The latest UFC fight odds price challenger Makhachjev as the narrow -260 betting favorite, with champion Della Maddalena a +215 underdog.

One thing that is for certain, however, is that the UFC absolutely loves putting on a marquee main event in the most famous arena on the planet. They’ve been running events in the Big Apple since 2016, and here are the first six main ones that took place inside Madison Square Garden.

Conor McGregor Becomes First Ever Champ-Champ

Back in 2016, Conor McGregor - fresh off back-to-back fights with Nate Diaz - looked to make history. The brash Irishman was already holding the featherweight title, and he challenged lightweight king Eddie Alvarez in a bid to become the first-ever simultaneous two-weight world champion in history. The Notorious One was up to the task.

In arguably the finest performance of his career, McGregor dismantled the Underground King, picking the champion apart with blistering counter strikes. He dropped Alvarez three times in the first round before delivering a brutal four-punch combination in the second to secure a knockout victory and crown himself the first-ever "champ-champ."

What’s your all-time favourite Conor McGregor fight? 🤔 pic.twitter.com/M1nNzbFPlz

— Bodog (@BodogCA) July 13, 2024

GSP Returns With a Bang

The following year, a long-anticipated clash between middleweight champion Michael Bisping and former welterweight dynasty Georges St. Pierre headed to Madison Square Garden. The two were supposed to face off four months prior, but an eye injury to Rush saw the bout postponed till November.

Once it did take place, St. Pierre proved why his name belongs on MMA's Mount Rushmore. Despite being out of action for four years before the contest, the Canadian hadn't missed a step, and he took the fight to Bisping, eventually securing a rear-naked choke in the third round and putting his British rival to sleep.

DC a Class Above Derrick Lewis

In 2018, Derrick Lewis secured a shock heavyweight title shot after viciously knocking out Alexander Volkov barely a month prior. Champion Daniel Cormier welcomed his compatriot to the elite stage, but ultimately showed the challenger no mercy. He submitted his heavy-hitting rival in the second round, securing a comprehensive victory.

Jorge Masvidal Crowned BMF

Throughout 2018 and 2019, journeyman Jorge Masvidal was on the greatest run of his career. Back-to-back knockouts of Darren Till and Ben Askren - the latter took just five seconds - caught the attention of superstar Nate Diaz. The Stockton native called out Gamebred after defeating Anthony Pettis in his return to action after the back-to-back bouts with McGregor, claiming that both he and Masvidal were the two "Baddest MFs" in the UFC.

The bout was duly signed, and the UFC pulled out all the stops, even creating a title belt to be awarded to the victor. On fight night, however, Masvidal was a different beast. He battered Diaz for three straight rounds, dropping him twice and opening up a huge cut over his eye. The cautious NYSAC then had a doctor evaluate Diaz, who deemed the Californian unable to continue, handing Masvidal a TKO victory, much to the annoyance of the 20,000 fans packed into MSG.

Usman and Covington Put on Another Classic

Back in 2019, Kamaru Usman knocked out Colby Covington in an all-time great main event in Las Vegas to defend his welterweight title. Two years later, the pair did battle once again inside Madison Square Garden, reigniting their bitter feud from before. And once again, the pair put on an absolute war. With both fighters having their moments, the judges awarded a narrow but deserved unanimous decision victory to the Nigerian Nightmare, ending the rivalry once and for all.

Alex Pereira Shocks the World

In 2021, Israel Adesanya had built up a stellar resume to become the longest reigning middleweight champion since the days of Anderson Silva. However, there was an Alex Pereira-sized asterisk next to his name. The Nigerian-born New Zealander was once knocked out by the Brazilian in the pair's kickboxing days, and after knocking out Sean Strickland, Pereira was given a title shot.

Many expected Adesanya to gain redemption and secure a victory of his own. He looked well on course to do exactly that as he dominated throughout the first four rounds.

However, in the fifth, Pereira backed the Last Style Bender up to the cage and unleashed a brutal attack, culminating with a vicious left uppercut that prompted the referee to step in and end the contest. Poatan secured the TKO victory, the middleweight gold, and cemented himself as one of the UFC's top stars, all in one night at Madison Square Garden.