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The Biggest Fights at Madison Square Garden

Dubbed the World’s Most Famous Arena, Madison Square Garden is the Mecca of sports. Nearly every great boxer has held a fight at this arena, from Muhammad Ali to Sugar Ray Robinson.

The Garden isn’t limited to boxing, though. Some of the most memorable UFC fights of the past decade were held at the venue. Then there’s the WWE, the NBA, and music artists from all walks of life.

In this article, we’ll focus on legendary fights that took place at the Madison Square Garden. Some of the fights took place long before you could stream fights online.

What’s more, you couldn’t bet on sports in the US. Now, not only can you stream sports, but you can also learn how to bet on sports in NY. Importantly, you can bet on sports through a variety of options. Let’s get started.

1: Muhammad Ali vs. Joe Frazier

Muhammad Ali made headlines in 1970 after announcing his retirement. Ali stepped away from boxing due to the controversies that arose from his decision not to serve in Vietnam.

Luckily, the Supreme Court cleared way for Ali to get back to boxing after ruling that young Americans could avoid the war on ethical grounds. “The Greatest” acquired his boxing license and agreed to fight Joe Frazier at the Madison Square Garden the same year (1971).

Ali came prepared to extend his perfect round to the then 27-year-old Frazier. He fought hard. But Frazier fought even harder. At the end of the 15-rounf fight, judges declared Frazier the winner unanimously.

Ali and Frazier would go on to fight in a trilogy that saw Frazier win the second fight but lose in the third meeting.

2: Connor McGregor vs. Eddie Alvarez

In 2016, Connor McGregor was at the top of his career. New York had just legalized mixed martial arts as a sport and the UFC wanted to show the world what MMA was all about.

Needless to say, Dana White booked the biggest fight of the year at the Garden. More than 20,000 people bought tickets to watch the fight live, with millions of others watching the game at home.

The fight between McGregor and Alvarez was special. It was a champion versus champion battle, with the winner getting a chance to hold two titles. The Irishman dropped Alvarez four times on the mat before winning comfortably.

3: Anthony Joshua s. Andy Ruiz

Before this fight happened in 2019, nearly every sportsbook tipped the Englishman to win. He was the heavyweight champion. Despite that, Ruiz floored him four times to take his IBF, WBA and WBO titles at the Madison Square Garden.

Joshua looked in control of the fight in the first three rounds. But after that, Ruiz did most of the hard work, hitting him left right and center. Being an unexpected loss, Joshua triggered a rematch the same year and won.

Unfortunately, Joshua’s luck didn’t last long. The next time he faced a strong opponent in Oleksandr Usyk of Ukraine, he lost. He requested a second fight, and lost once more.

#4: Evander Holyfield vs. Lennox Lewis

When the first match between Tyson Fury and Deontay Wilder ended in a draw, many Britons were reminding of a similar match that took place in 1999. At the Madison Square Garden, Britain’s Lennox Lewis had a match against American Evander Holyfield.

At stake were three belts, two held by Holyfield (WBA and IBF) while Lewis held the WBC title. The referee of the match was Arthur Mercante Jr, a man whose father had officiated the fight between Ali and Frazier.

The two men fought hard. But for everyone watching the fight at home, there was one clear winner: Lewis. Sadly, the judges had a different opinion. They ruled the match a draw, causing a backlash that forced then New York mayor Rudy Giuliani to call the ruling a “highway robbery.”

Luckily for Lewis, he got his revenge eight months later. He fought Holyfield in a rematch where he was ruled the winner. Interestingly, some critics argued the American had done well-enough for the fight to be ruled as a tie.

#5: Jake LaMotta vs. Sugar Ray Robinson

In 1942 in New York, boxing hall of famers Jake LaMotta and Sugar Ray Robinson started a feud that would last nine years. The match was a non-title middleweight bout that ended with a victory for Sugar.

LaMotta booked a rematch the following year and won. This was the only fight jake won. After that, Robinson dominated all other fights, including the 1951 “Saint Valentine’s Day Massacre.”

Although both fighters are legends of the sport, Robinson had the more illustrious career. Of the 200 professional fights he fought, he won 173 of them. He knocked out his opponents 108 times, and never got knocked out. However, he once lost a fight due to heat exhaustion at the Yankee Stadium.

#6: Jorge Masvidal vs. Nate Diaz

Both Masvidal and Diaz are the tail end of their careers. In 2019, though, both MMA champions were fighting for the BMF title. At the start of the match, it looked like anyone might have won.

Then Masvidal hit Diaz hard enough to cause a cut that warranted a stoppage by a doctor. Masvidal was inevitably declared the winner. Interestingly, a rematch between the two MMA athletes has never been actualized four years later.

#7: WrestleMania I and X

In 1994, the WWE returned to Madison Square Garden in a fight headlining Shawn Michaels and Razor Ramon. WrestleMania began at the MSG after all.

During the first ever WrestleMania event in 1985, Hulk Hogan teamed up with Mr. T to fight the duo of Paul Orndorff and Roddy Piper. Although thig fight was epic, it was overshadowed by a litany of celebrities like Muhammad Ali, and Cyndi Lauper who attended the event.

In WrestleMania X, the main event was free of celebrity shenanigans. Michaels faced off Ramon to lift off the unifying Intercontinental championship belts hung above the ring.

Ramon and Michaels battled for the better part of the night. But in the end, bad guy Ramon pushed Shawn off the ladder and lifted the belts.