How Floyd Mayweather vs Conor McGregor is far from the first boxing vs MMA 'freak show'

Muhammad Ali, James Toney and Kimbo Slice have all been involved in memorable boxing vs MMA clashes — with varying degrees of success

The reason Floyd Mayweather’s forthcoming fight with Conor McGregor is so eagerly anticipated is not because it’s expected to be a particularly close contest – the American can currently be backed at odds as short as 1/7 – but because fight fans are intrigued as to how well the skills of a mixed martial artist will translate in the boxing ring.

McGregor is known as one of the greatest strikers in the UFC, with few of his opponents unable to survive his devastating pull-back left-hand counter. But how quickly will the Irishman have learnt the many nuances of boxing, with a set of skills that Mayweather has honed day in, day out for the past 30 years?

But McGregor is far from the first fighter to chance his arm in a different sport. From Muhammad Ali to Kimbo Slice, Ray Mercer to James Toney – the two sports of boxing and MMA have often found themselves entwining in surprising new ways.

Here, we run through some of the most memorable boxing vs MMA clashes.

Muhammad Ali vs Antonio Inoki

Ali took place in a bizarre crossover clash (Getty)

It’s often forgotten that even The Greatest took part in a bizarre mismatch of boxing vs MMA. In 1976, as Ali’s storied career was beginning to approach the end, he agreed to face Japan’s biggest pro wrestling star. Why? “Six million dollars, that’s why,” was his now legendary reply.

But the fight was a farce. Inoki was on his feet for the first 14 seconds of the very first three-minute round, and then lay flat on his back throughout. His approach to the fight meant that it took until the seventh round for Ali to throw his first punch. He would throw five more before the fight was declared a draw, with the two making hasty exits from the ring amid a chorus of jeers.

Royce Gracie vs Art Jimmerson

A national Golden Gloves middleweight champion as an amateur and riding a 15-fight win streak in his normal sport, Art Jimmerson was no joke. Unfortunately, UFBut MC 1 was. The tournament of clashing styles pitted the boxer against Brazilian jiu jitsu star Royce Gracie, and when the fight went to the mat, Jimmerson had no chance.

Bizarrely, Jimmerson fought with only one glove on, after future UFC ref John McCarthy told him it could be difficult for the referee to spot him tapping out wearing a heavy boxing glove. That’s exactly how the fight ended — although Jimmerson was clearly intrigued by his first foray into MMA. He now works as the head boxing coach at the UFC Gym in Torrance, California.

Ray Mercer vs Tim Sylvia

The fight between former world heavyweight boxing champion Mercer and reigning UFC heavyweight champ Syliva was meant to be a boxing match. But the New Jersey state athletic commission refused to sanction it, forcing a move into the cage, with 4 oz gloves.

Ahead of the fight there was a gentlemen’s agreement between the pair that they would only throw punches at one another, thus rendering the contest a de facto boxing match. But it took Sylvia just seconds to break that agreement, when he struck Mercer with a hard inside leg kick.

Mercer’s response? A booming overhand right before two more lighting quick rights on the mat. The boxer won via KO.

Kimbo Slice vs Brian Green

Kevin Ferguson aka Kimbo Slice found fame during the early days of YouTube, as videos of his brutal back-alley brawls began to go viral. He then decided to dip his toe into the world of professional MMA — with mixed results — before embarking on a boxing career.

In his fourth pro fight, he found himself up against Green, a middleweight MMA fighter making his ring debut. Despite being by far the smaller man, Green dominated the first three-and-a-half rounds and looked to be on the path to victory. But with just seconds left on the clock, Kimbo landed a stinging combo which floored his rival.

Kimbo also tried his hand in professional MMA (Getty)

Ricardo Mayorga vs Wesley Tiffer

When Mayweather declined the opportunity to meet McGregor in the Octagon, perhaps he had the sorry career of Ricardo Mayorga in his mind. The Nicaraguan former lineal welterweight champion was a big star in boxing when he decided to give MMA a go, known for his relentless trash-talk and 20-a-day smoking habit as he was for his long list of knockout victories.

His first fight in the cage got off to a reasonably promising start, as he finished Wesley Tiffer, but his win was turned into a no-contest because of an illegal knee into Tiffer’s spine. Undeterred, Mayorga would make three more appearances in the cage, but lost them all.

Randy Couture vs James Toney

Toney had more success in the ring than the Octagon (Getty)

If McGregor is the most talented man to switch from MMA to boxing, James ‘Lights Out’ Toney is the most talented man to switch the ring for the Octagon. He’s also almost as loud-mouthed as the Irishman, infamously branding UFC president Dana White “a straight-up ho” in order to land his shot in the MMA game.

It took Couture — a former UFC heavyweight and light-heavyweight champion and the first man in the history of the promotion to hold world titles in two different weight classes — just 15-seconds to secure a takedown. Toney was able to hang on in there for a while, but eventually lost via an arm-triangle choke after three minutes and 19-seconds.

And all the fights that never happened…

Perhaps the greatest boxing vs MMA clash that never took place is Anderson Silva’s much-mooted fight against Roy Jones Jr. The pair came close to a money-spinning clash in 2008, only for negotiations to unfortunately break down.

Meanwhile former heavyweight champion of the world Tyson Fury has boldly declared that he could beat Cain Velasquez in the Octagon, while Jimi Manuwa has been busy calling out David Haye in recent weeks. And just a few weeks ago, the British light-heavyweight contender revealed there had been a conference call between the two men and Dana White.