Whenever the UFC is hosted at Madison Square Garden, it always produces one of the most anticipated events of the year.
Time after time, we have seen some of the biggest matchups in UFC history take place in the iconic arena.
Every main event that has taken place at MSG has arguably delivered, although some battles have ended with disappointment.
Before the super-fight between Jack Della Maddalena and Islam Makhachev takes place in the headliner of UFC 322, here are all previous main events ranked from worst to best.
UFC 230: Daniel Cormier vs Derrick Lewis
We go back to 2018 when Cormier was a simultaneous two-division champion, holding the heavyweight and light heavyweight titles.
‘DC’ won the 265lbs belt when he knocked out Stipe Miocic at UFC 226 and was set for his first defence in MSG.
Lewis fought in the same event against Francis Ngannou, which was prepared to be an exciting battle, but ended as a ‘borefest’, although he did win by unanimous decision.
Before his title fight, ‘The Black Beast’ fought Alexander Volkov and earned a comeback knockout win in round three at UFC 229.
It was a battle that came together quickly, as Lewis had less than a month to prepare for his title shot, not providing a huge build-up for fans.
As no surprise, Cormier was heading into the title clash as a heavy favourite, hoping to secure his third win of the year.
The heavyweight champion claimed a comfortable win, submitting Lewis with a Rear-Naked Choke in round two.
Surprisingly, this would be Cormier’s last victory before retiring from mixed martial arts.
UFC 309: Jon Jones vs Stipe Miocic
In 2023, Jones vs Miocic was booked as the headliner of UFC 295, with fans calling it the biggest heavyweight title fight in history.
However, due to injury, Jones had to pull out, and the main event was scrapped and rescheduled a year later.
By the time it came to UFC 309, Jones had not fought in 20 months, and Miocic had not been active since March 2021.
Not to be forgotten, Tom Aspinall became the interim champion and defended the title before this matchup was scheduled.
It seemed obvious to many of the MMA community that ‘Bones’ would clearly win since Miocic had not been victorious since August 2020.
This led many fans to speculate that the scheduled five-round heavyweight title fight would not last long.
In the end, Jones won by third-round knockout after a brutal spinning back kick to the body, making it his first successful title defence at 265lbs.
While it was no surprise that the two-division champion won, fans were more focused on who Jones’ next opponent could be, until his retirement was confirmed in June this year.
UFC 295: Jiri Prochazka vs Alex Pereira
Initially set as the co-main event, Prochazka vs Pereira was moved to the headliner for the vacant light heavyweight belt.
The Czech fighter had not competed since his title triumph against Glover Teixeira at UFC 275.
Pereira earned his shot for the light heavyweight title after edging a split decision over former champion Jan Blachowicz at UFC 291.
The new headliner for UFC 295 became more exciting since both men were spectacular knockout artists.
In his seventh UFC bout, ‘Poatan’ was aiming to become a two-division champion after previously winning the middleweight title against Israel Adesanya.
Prochazka had not been beaten since December 2015, making this championship contest so hard to predict.
Pereira won by second-round TKO; however, some of the MMA community believed it was a bad stoppage as Prochazka quickly rose to his feet when the bout was stopped.
Despite the premature ending, both fighters would face off again in a rematch at UFC 303, with Pereira winning again by second-round TKO.
UFC 244: Jorge Masvidal vs Nate Diaz
The inaugural BMF title was up for grabs in MSG as two of the most loved UFC fighters would try to win the prestigious prize.
Masvidal stunned everyone in his previous fight when he knocked out Ben Askren in five seconds at UFC 239.
Diaz defeated Anthony Pettis in his return to MMA and called out ‘Gamebred’ to battle for the BMF title after his stunning performance.
A guaranteed fun fight would become the headliner for UFC 244, seeing who would be the ‘baddest motherf***er’ of the UFC.
The welterweight contest provided fireworks with both men trading strikes in an eye-catching battle.
Masvidal inflicted damage on Diaz, knocking down the Californian twice within three rounds out of five.
Just as the fourth round was ready to begin, the doctor checked the cut above the eye of Diaz and forced the bout to be stopped, leaving everyone in frustration and disappointment.
The Miami-born fighter became the BMF Champion, winning by TKO (Doctor’s Stoppage), certainly not how he would have liked the fight to end.
UFC 268: Kamaru Usman vs Colby Covington 2
UFC 268 has been regarded as one of the greatest MMA events due to the countless entertaining battles and incredible knockouts.
However, the headliner could not have capped it off any better in a satisfying rematch between Usman and Covington.
Their first matchup took place at UFC 245 with the ‘Nigerian Nightmare’ winning by fifth-round TKO and earning his first title defence.
Covington had the opportunity to claim revenge after he redeemed himself with a TKO win against Tyron Woodley.
The five-round contest was certainly a crowd-pleaser as both men landed a combined total of 277 strikes.
Usman had the upper hand in the battle, landing two knockdowns as he came close to finishing the fight.
By the end of the championship clash, spectators were standing and applauding the two fighters for their warriorship.
The welterweight champion retained his title but would give plenty of respect to Covington after a gruelling battle.
UFC 281: Israel Adesanya vs Alex Pereira
One particular attribute which makes a rivalry so good is history, and that’s exactly what the headliner had at UFC 281.
Adesanya had faced Pereira twice in Kickboxing at Glory of Heroes (GOH), with the Brazilian winning the first bout by unanimous decision and the second by third-round knockout.
Since then, ‘The Last Stylebender’ has positioned himself as one of the greatest in UFC middleweight history.
Meanwhile, Pereira paced his way to a title shot within a year after victories over Andreas Michailidis, Bruno Silva and Sean Strickland.
The championship fight almost went the distance, although it nearly ended in the first round when Adesanya rocked Pereira right at the end of round one.
The champion was getting the better of the challenger in terms of strikes and grappling, as he was ahead on the scorecards.
During round five, Pereira stunned Adesanya with a vicious left hook before firing an arsenal of strikes to stop the bout and complete the comeback.
Just like that, Pereira became the new UFC Middleweight Champion and became the first to defeat Adesanya at 185lbs in MMA.
UFC 217: Michael Bisping vs Georges St-Pierre
It’s not often you see three title fights in one UFC event, especially three new champions in one night, which happened at UFC 217.
‘GSP’ made his return to MMA after four years away from the Octagon since his split decision win against Johnny Hendricks.
Bisping avenged one of his iconic losses against Dan Henderson in his previous fight, winning by unanimous decision to defend the belt.
While the build-up and attention focused on the return of St-Pierre, ‘The Count’ certainly boosted viewership with his pre-fight trash talk.
Questions arose about whether the Canadian still had what it takes to be a champion after his four-year layoff.
And they were answered as St Pierre made the crowd go wild in round three when he knocked down the Briton.
Eventually, after taking the back of Bisping, GSP submitted Bisping unconscious with a Rear-Naked Choke to become the new middleweight champion.
This made St-Pierre a two-division champion and cemented him as the greatest to achieve this feat in MMA.
UFC 205: Eddie Alvarez vs Conor McGregor
The first-ever MSG event in UFC history provided one of the most iconic moments in the sport.
Alvarez made his first title defence after winning the belt from an emphatic first-round TKO win over Rafael dos Anjos.
McGregor was hunting for success, which no one had ever achieved before, as the featherweight champion was hoping to add a second title to his collection.
Of course, at this time in November 2016, ‘The Notorious’ had a huge fan base behind him, which guaranteed a fascinating build-up.
McGregor displayed nothing but dominance in his first UFC lightweight clash, causing multiple problems for Alvarez.
The Irishman knocked down the champion twice in round one, coming very close to finishing the fight.
With two minutes left of round two, the featherweight champion landed his third knockdown and secured a second-round TKO title triumph.
It was the first time a fighter had ever become a simultaneous two-division champion as McGregor pulled off one of the greatest moments in UFC history.
