Mayweather vs. McGregor: When MMA Meets Boxing

Mixed martial artists and sweet scientists have crossed sporting boundaries to compete for decades, but the results have rarely been anything other than disastrous…

Proto-MMA

Muhammad Ali vs. Antonio Inoki

The year was 1976. Muhammed Ali was a year removed from winning the legendary Thrilla in Manila against Joe Frazier and he was on something of a retirement tour. So why did he break from going through the motions against overmatched opponents to fly to Japan and ‘fight’ pro wrestler Antonio Inoki? “Six million dollars, that’s why,” explained ‘The Greatest’.

Accounts vary about whether this was supposed to be a choreographed exhibition or a legitimate contest, but there is no denying it ended up being a complete debacle. A sold-out crowd at Tokyo’s Budokan – and millions watching across the globe – saw the world heavyweight boxing champion throw a total of six punches across a total of 15 rounds, while Inoki mostly lay on his back and kicked the icon’s legs. The circus was declared a draw and both fighters left embarrassed, but considerably richer.

One mitt and quit

Royce Gracie vs. Art Jimmerson

Possibly the most infamous example of a disastrous boxing collision with MMA came in the very first UFC event. Few people really knew what was going on in this tournament of style vs. style vs. style, but one thing they could be certain about was that this boxer with one glove didn’t have any idea what he was letting himself in for.

Art Jimmerson might have been 29-5 as a pugilist when he entered the Ultimate Fighting Championship, but you could bet good money his Brazilian jiu-jitsu experience was non-existent. Rarely has a man seemed so terrified when he was taken off his feet, put on his back and left with just one mitten free to defend himself. As soon as Royce Grace took mount, ‘King Arthur’ tapped in desperation for it all to be over.

Old dog, old tricks

Ray Mercer vs. Tim Sylvia

Despite Ray Mercer boasting an Olympic gold medal from the 1988 Seoul Games and a short stint as WBO heavyweight champion, most people thought he was doomed walking into a cage with six-foot-eight Tim Sylvia. The fight was originally supposed to be a boxing match, but no commission would sanction it, forcing a change to MMA rules and 4oz gloves.

Furthermore, the former boxer was 48 years old, it was his pro debut and his only previous MMA experience was being submitted by Kimbo Slice in an exhibition match. There was talk of a gentleman’s agreement to stick to punching exchanges, but ‘The Maine-iac’ broke that immediately with a tentative inside leg kick. ‘Merciless’ gave him an angry look and threw a vicious overhand right. The two-time UFC heavyweight champion toppled over in slow motion and ate two more right hands to complete his humiliation.

Exposed in the ring

Kimbo Slice vs. Brian Green

Once it was undeniable that the world’s most famous backyard, boatyard and basement brawler wasn’t cut out for MMA, Kimbo Slice turned his attention to boxing. He didn’t challenge himself all that much, taking four-round fights against opponents with a combined 2-5 record in his first three contests.

His fourth was against Brian Green, a middleweight MMA submission specialist making his ring debut who later admitted to wearing 20lb ankle weights to meet the heavyweight requirement. Kimbo should have won at a canter. Instead, Green lit him up for three-and-a-half rounds and brought the streetfighting star to within moments of an embarrassing defeat. However, with three seconds to go, Kimbo landed a three-punch combo that floored Green and saved his skin.

Legends’ match

Anderson Silva vs. Roy Jones Jr.

Regarded by some as the greatest fighter of all-time, surely Anderson Silva would have excelled in any combat realm he dipped his toe into? Not so. ‘The Spider’s boxing record is as unremarkable as his MMA career is remarkable: two fights, seven years apart, one win, one loss.

That did not, however, stop discussion of a boxing match with Roy Jones Jr. when the former middleweight champ was enjoying his best bobbing, weaving and knockout form. A fight between the former pound-for-pound boxing king and MMA’s then-leader would have been box office gold, but the appetite for cross-sport promotion was not at Mayweather-McGregor levels in 2008. The pair have amiably angled for a fight ever since, but are still yet to face off.

No chance

Randy Couture vs. James Toney

James ‘Lights Out’ Toney was the first world-class boxer to fight in the UFC. He was also undoubtedly the most accomplished and talented man to ever make the jump from his sport into MMA – a defensive master and former lineal middleweight champion.

He made a lot of noise, including calling Dana White a “straight-up ho”, to get his chance in the Octagon. The trouble was, when he signed up to fight Randy Couture at UFC 118 he was a long way removed from his prime. He was 42 years old, 237lb and he had no idea what grappling or kicking involved. “Front kick, back kick, all that… Side check kick,” he responded when the UFC President asked if he’d worked on leg kicks.

Predictably, Randy Couture took him down after 15 seconds with one of the most telegraphed single-legs ever seen in a cage, beat him mercilessly for three minutes and choked him out.

Wild bull

Ricardo Mayorga vs. Wesley Tiffer

Wherever Ricardo Mayorga goes, controversy usually follows. The Nicaraguan was a big ticket at the start of this century, his raging aggression and exhilarating offensive fighting style combined with ferocious trash talking, a 20-a-day smoking habit and hard-drinking lifestyle made him a unique proposition among world-class fighters.

His 2013 foray into MMA was bound to generate attention, even though his first, failed, attempt ended before it began thanks to an injunction from Don King. Alas, the headlines he made were all negative.

‘El Matador’ came into his fight at Omega MMA: Battle of the Americas 20lbs overweight and had his win overturned to a no-contest due to an illegal knee. Three more fights followed that year. All ended in defeat.

Striking scientist

Holly Holm vs. Ronda Rousey

Before she diversified her athletic career, Holly Holm had already reached the top in the boxing ring with titles in three weight classes and recognition as the top pound-for-pound athlete in the women’s game. But she was always far more than just a pure boxer. A background in kickboxing and a home base in Albuquerque, New Mexico with Jackson-Wink MMA set her up for success after she called it a day in the ring.

Ten fights into her career, she caused one of the greatest upsets ever by beating undefeated Ronda Rousey by brutal head-kick KO in an Australian stadium. ‘The Preacher’s Daughter’ earned a record four World MMA Awards prizes for her accomplishment.