Bizarre Floyd Mayweather Fights That Shouldn’t Have Happened

Published 01/08/2022, 2:30 PM EST
LAS VEGAS – AUGUST 24: Boxer Floyd Mayweather Jr. (L) stares down wrestlers Chris Jericho and Big Show during the WWE Monday Night Raw show at the Thomas & Mack Center August 24, 2009 in Las Vegas, Nevada. Mayweather was a special guest host during the broadcast. (Photo by Ethan Miller/Getty Images)

Floyd Mayweather, one of the greatest boxers who perfected the art of defense and counter-punching that made him nearly untouchable during his career. Although he did not have one-punch knockout power, he would destroy his opponents slowly round after round.

In a career spanning over two decades, Mayweather has fought some of the best fighters of his era. From Manny Pacquiao to a young Canelo Alvarez.

Jun 3, 2021; Miami Beach, Florida, USA; Professional boxer Floyd Mayweather Jr. looks on after the face off with YouTube star Logan Paul at Villa Casa Casuarina. Mandatory Credit: Jasen Vinlove-USA TODAY Sports

He has also fought some of the most bizarre opponents during this time. Let’s look at Floyd Mayweather‘s most bizarre fights:


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Floyd Mayweather vs Conor McGregor 

In one of the most bizarre crossover events, the UFC’s pay-per-view king took on the king of boxing. Conor McGregor kept calling ‘Money’ Mayweather out to fight him in the boxing ring. ‘The Notorious’ Conor McGregor had one of the best striking skill sets in the UFC and wanted to take on Mayweather.

After a lot of back and forth, the pair faced each other on August 26, 2017. Despite what boxing pundits predicted, Conor McGregor held his own in the boxing ring and won the first three rounds before gassing out and getting stunned by Mayweather in the 10th round.

Floyd Mayweather vs The Big Show

Although not a boxing fight, yet another bizarre crossover event was when Mayweather took on ‘The Big Show’ at WrestleMania 24 on 30 March 2008. The 5 foot 8-inch, 145-pound boxer took on the 7-foot one-inch 441-pound wrestler in one of the most bizarre fights ever.

Despite the size and weight disadvantage, Mayweather landed multiple chair shots that hurt The Big Show, then finished him by knocking him out with brass knuckles.

Floyd Mayweather vs Tenshin Nasukawa

On December 31, 2018, a 41-year-old out of shape, Floyd Mayweather took on an unbeaten Japanese MMA prospect in an exhibition fight. Mayweather took the fight as a joke and toyed with his opponent. The promoters set the fight for three rounds. Mayweather, however, needed only one to show his class.

In the very first round, after toying with Nasukawa for a while, Mayweather switched gears and knocked him down thrice before his corner threw the towel in.


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Floyd Mayweather vs Logan Paul 


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In his most recent fight, ‘Money’ Mayweather took on YouTuber turned boxer Logan Paul for an eight, three-minute round exhibition fight. To Paul’s credit, he went the distance with one of the greatest boxers in the world, despite having a great reach and weight advantage.

Mayweather clearly outboxed ‘The Maverick’, but the promoters decided not to announce a winner at the end of the fight. Despite a valiant effort, Paul came nowhere near threatening Mayweather’s unbeaten record.


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Which opponent do you think was the most bizarre out of these with whom Floyd Mayweather fought? Let us know in the comments section below.



Allan Binoy

578 articles

Allan Binoy is a Boxing writer at EssentiallySports. Currently pursuing a Bachelor's degree in English Literature from Loyola College, Allan fuses his love for literature and the sport of boxing to deliver quality copies about 'The Sweet Science.' Allan is a semi-professional soccer player for Diego Juniors FC.