6 Cross-Combat Fights That Paved The Way For Mayweather vs McGregor

6 Cross-Combat Fights That Paved The Way For Mayweather vs McGregor

A money making spectacle, a dream fight, an answer to the "what if" question of the century, or a complete farce? Everyone has their opinion on Conor McGregor and Floyd Mayweather's fight this Saturday. When it's all done, will any of these opinions be swayed? That's not clear.

While the fight is certainly regarded as an abomination by some, it is far from the first of its kind.

Many fighters of different codes have crossed over into different disciplines, either to challenge themselves, prove their sport is superior, or just take a pay day. Without these clashes though, we might not have the basis for Mayweather vs McGregor, even many of them merely prove the adage: when an apple fights an orange, the only result can be a fruit salad.

Floyd Mayweather vs. The Big Show

WrestleMania 25, 2008



It was only a matter of time before Mayweather entered into the world of professional wrestling given his ability to run his mouth and his brash ego. WWE decided to pit him against The Big Show, dubbing their feud as “The Best versus The Biggest”, but made the initial error of having the boxer play the good guy. Mayweather was so unlikable and obnoxious to the wrestling audience that they quickly had to turn him heel.

At No Way Out 2008, Mayweather punched Show in a promo, legitimately breaking the wrestler’s nose in the process. Turns out the big man had asked the undefeated fighter to hit him for real, causing blood to stream from his face on live television. That set up their match a month later, which would last roughly ten minutes and was a lot better than people expected. After punching Big Show with brass knuckles to get the win, commentator Michael Cole gleefully told viewers that Mayweather’s record was now 40-0. That win mysteriously disappeared from Floyd's record thereafter. 

Butterbean vs. James ‘The Collossus’ Thompson

Born 2 Fight, 2007



A cult hero among fight fans, Eric Esch fought over a hundred times and possessed a ferocious right hook. Commonly known as Butterbean, it’s difficult to pick just one of his forays into various combat sports as he’s had so many of them. He’s fought professionally in both kickboxing and MMA, and has also fought at WrestleMania, although unlike Mayweather it was a legitimate shoot fight.

The biggest win of the American’s eight year career in MMA came against Pride veteran James Thompson at a Cage Rage event in Wembley Arena. The trash talking Thompson taunted the 170kg boxer with highly original jibes about eating McDonalds, but couldn’t make it past 43 seconds of the contest. Esch won 17 fights in his MMA career with 10 submissions and six knockouts to boot.

Antonio Inoki vs. Muhammad Ali




Hyped as the bout of the century, Ali went to Tokyo to take on wrestling legend Inoki in a fight that presaged mixed martial arts, but it was anything but. Instead of getting a pure boxing vs wrestling battle, a special set of rules were established; there was to be no kneeing, kicking, or hitting below the belt. Ali would be wearing four-ounce gloves, while the Japanese would go bare-handed. This was demanded by Ali’s camp after discovering the match-up would be a legitimate fight and not a work.

The resultant contest was a farce. Inoki, doing his utmost to avoid Ali’s fearsome punches, spent the vast majority of the 15 rounds on his back, attempting to sweep his opponent with leg kicks. At one point when an actual fight threatened to break out via some grappling, Inoki ended up squatting on Ali’s face. Through the indignity of it all he had only thrown six punches.

At 33 years of age at the time, The Greatest had intimated he was close to retirement (he in fact wouldn’t retire until 1981) and when asked in a press conference why he was taking the fight, he answered “six million dollars, that’s why.” The parallels with Mayweather vs McGregor are plain to see four decades on.

Side note: the fight was refereed by Gene LeBell, who invented the Yes Lock made famous by former WWE wrestler Daniel Bryan.

Randy Couture vs. James Toney

UFC 118, 2010



As MMA has shot into the mainstream consciousness over the past few years, and with boxing on a seemingly constant slide, the debate over which is better hasn’t so much been settled as it has just vanished into the ether. At its height though, there were plenty of boxers looking to get inside the octagon as they sought a payday.

James Toney was one such man, who announced his willingness to cross into the cage at a UFC event. Dana White quickly capitalised on the opportunity and set up a clash with hall of famer Randy Couture at UFC 118. The boxer was taken down by the 47-year-old after 15 seconds and had no answer for the veteran’s ground game. It was desperately disappointing to see a man with dozens of knockouts to his name submit without throwing a single punch. This went closer than any fight to deciding which sport is better.

‘Merciless’ Ray Mercer vs Tim Sylvia

Adrenaline III: Bragging Rights, 2009


The MMA career of Ray Mercer was short but spectacular. The American had an impressive boxing record, losing just seven of his 44 pro fights, winning the WBO heavyweight title in 1991 after grabbing gold at the 1988 Seoul Olympics. So naturally, at the age of 46, he decided to step into the world of MMA.

Mercer’s first fight ended with a first round submission loss at the hands of Kimbo Slice at a Cage Fury event, after which he bizarrely admitted that he didn’t really train in any other aspect of MMA, and was completely unprepared for the guillotine choke that downed him. Two years later he fared a lot better in his second and final MMA bout, knocking out Tim Sylvia after just 9 seconds in a shock victory. It was the former UFC heavyweight champion’s first ever defeat by knockout.  

Art Jimmerson vs Royce Gracie

UFC 1, 1993


This fight has gone down in MMA history, but not simply because it was boxer versus martial artist.

Art Jimmerson went into the inaugural Ultimate Fighting event looking to earn enough money to buy a house. A journeyman boxer with zero experience of the ground game, Jimmerson chose to start the fight with one boxing glove on. It was a sight to behold, but a pretty embarrassing one at that.

It was thought that Jimmerson only wore the one glove in order to keep a hand free for grappling, but it was revealed in a 2013 interview with Campbell McLaren, the first executive producer of UFC, that it was for other reasons.

“He decided to wear the one glove," McLaren revealed, "to make sure we could see him tapping with the other hand. Walking with him to the Octagon, he said, 'If I tap with my glove hand, is it a still a tap?' That's when I knew it wasn't going to work out."

Unsurprisingly, Jimmerson tapped out within two minutes to the Jiu-Jitsu black belt, but his name will be forever enshrined in mixed martial arts folklore.

Special mention to Royce Gracie's battle with sumo wrestler Akebono, which just missed the cut.


It will be interesting to see where Mayweather vs McGregor will fall in the patheon of cross combat fights? It's certainly the biggest, but will it be the best. A common thread through this article has been boxers going into other fields, perhaps underestimating their opponents and their sport. Are MMA fans and Conor McGregor underestimated and disrespecting the sport of boxing in a similar way this time out?


Ste McGovern
Article written by
A man and his cans. @nostalgiaultra5

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