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Mayweather vs McGregor: The Top 5 Combat Crossovers In History

"All these rules, all these restrictions, it doesn't faze me; it amuses me. It is funny to me all these rules. " - Conor McGregor


With the hugely anticipated showdown between the undefeated Floyd Mayweather and UFC superstar Conor McGregor just weeks away from becoming possibly the highest grossing boxing match in the history of the sport, the combat world is divided. Questions are arising as to whether this will potentially be the most exciting match up in recent history, or a one sided exhibition bout signed for nothing more than a pay cheque for both men.

The world of boxing was shaken up in June, when the recent rumours were confirmed and Showtime officially announced that the bout would take place in Las Vegas on August 26. From armchair fans to former world champions, social media went viral with farcical cries of outrage and excitement at the thought of McGregor making his boxing debut against a man who many claim to be the greatest defensive boxer in history. A man who has not only defeated 24 world champions in his 49 fight reign, but has never been dropped let alone lost a bout. Others claimed that the Irishman had an advantage and a world tour immediately followed to promote the match up, with the trash talk beginning in Los Angeles and ending in London, drawing in crowds larger than the fight itself can fit inside of the T-Mobile Arena.

So much talk from all angles has clouded the memories of fight fans, with many forgetting that there have been plenty of other famous crossover fights over the years. Although none will ever match the financial gain of the so called ” Money Fight” between Conor McGregor and Mayweather, there are a few honourable mentions of men who decided to step out of their comfort zones and experiment with another combat sport. There is a reason many fans forget these fights, as most were a gruelling representation as to why fighters should compete in their trained disciplines, and most concluding with an expected outcome.

Anyway, here are the top 5…

  1. 1 Randy Couture vs James Toney


    James Toney has had an exceptional career in boxing, having won world titles at middleweight, super-middleweight, cruiserweight and even heavyweight. Before the latter fight being scored a no contest due to a failed drug test post-fight by Toney, he decided to compete in Mixed Martial Arts after a meeting with Dana White at UFC 108 turned into a three-fight deal. 

    His opponent at UFC 118 was hall of famer Randy Couture, a two-weight champion, who is highly regarded as a pioneer in the sport. He took Toney down in under 20 seconds and submitted the 42-year-old inside the first round. Toney claimed after the fight that Couture took him down because he was scared, and unsurprisingly he was released from his contract.

  2. 2 Tim Sylvia vs Ray Mercer


    There was an unexpected turn of events when former UFC champion Tim Sylvia met with professional boxer Ray Mercer under MMA rules. The bout ended in only nine seconds after the boxer stunned the world of mixed martial arts by knocking out a former UFC champion inside the octagon. Although he had won in devastating fashion this was to be his only professional fight.

  3. 3 Eric "Butterbean" Esch vs Bart Gunn


    Although the event was held on a WWE PPV, it was labelled the " Brawl For All" as wrestlers fought legitimate fights in a tournament that resulted in the match up between professional boxer Eric " butterbean" Esch, Bart Gunn, and an unsurprisingly devastating knockout of the WWE star inside 40 seconds. 'Butterbean' would continue a prosperous career in both mixed martial arts and boxing, racking up a professional boxing record of 77 wins (58 KO's) and 17 wins in mixed martial arts, even giving kickboxing a try.

  4. 4 Kimbo Slice vs Tank Abbott


    Kimbo Slice became a world wide superstar through his early videos of backyard brawling, using only bare knuckle hands often ending in devastating knockouts. As his popularity grew he utilised his fighting skills to compete professionally. 

    Having won his debut against Ray Mercer, he proceeded to call out Tank Abbott, and after negotiations the two met in the octagon. Slice demolished the former UFC star with strikes within one minute of the first round and continued to fight until his death in 2016.

  5. 5 Muhammad Ali vs Antonio Inoki


    Muhammad Ali faced professional wrestler Antonio Inoki under special rules in Tokyo. The match-up itself was regarded as a flop and the fifteen round bout consisted of Inoki laying on his back kicking the legs of Ali, as the heavyweight boxer taunted him by shouting "coward" as he attempted to stay out of reach. Ali did not throw a punch for the first seven rounds and the match ended in a 15 round draw, with many spectators demanding their money back due to a poor display from both fighters. 

    Inoki later became involved in politics and negotiated the rescue of 38 hostages with Saddam Hussein during the gulf war. Ali stayed fond of his opponent claiming "Antonio Inoki and I put our best efforts into making world peace through sports, to prove there is only one mankind beyond the sexual, ethnical or cultural differences."

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Vuk Bobic

I am a UK based content writer, a boxing enthusiast, with a 'dabble' in MMA.

  • Craig Haldane

    Nice one man I enjoyed reading that

Mayweather vs McGregor: The Top 5 Combat Crossovers In History

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