Mike Tyson

From Mike Tyson vs Roy Jones to Floyd Mayweather, Evander Holyfield and even an octopus – boxing’s ten craziest exhibitions ranked

Mike Tyson, Muhammad Ali, Oscar De La Hoya and even an octopus all feature in talkSPORT's top 10 countdown of the weirdest, wildest boxing exhibitions ever to take place.

Floyd Mayweather’s global tour – including taking on former Geordie Shore ‘star’ Aaron Chalmers in London – and Manny Pacquiao entering the fray have popularised the unusual exhibition circuit. As have battles between YouTubers and reality TV stars.

Mayweather is coming back for another exhibition against Aaron Chalmers in London on February 25

Mayweather is coming back for another exhibition against Aaron Chalmers in London on February 25Credit: Sean Michael Ham/ Mayweather Promotions

But below are the most outlandish exhibition contests, each involving at least one actual pro athlete (no offence, KSI vs FaZe Temperrr) and discounting all official bouts. For example: Freddie Flintoff’s heroic win against Richard Dawson was a licensed pro contest, giving Fred a perfect 1-0 record. Whereas these 10 fights were strictly off the record.

10. Mike Tyson vs Roy Jones (2020)

At 10th because it’s relatively ‘normal’ to have two American superstar boxers slug it out, even if both were in their 50s, peaked several decades earlier, and Tyson was a natural heavyweight while Jones was at his best at 168lb.

The craziness came in with how successful this was: 1.6million PPV buys in the US alone, raking in $80million. The fight saw ‘Iron Mike’ actually do a good impression of his prime moves, outlanding Jones throughout. Yet it was declared an unofficial draw after eight two-minute rounds thanks to Vinny Paz’s bizarre 80-76 score for Jones (Christy Martin’s 79-73 for Tyson was a better take).

Tyson and Jones Jr made major headlines with their exhibition

Tyson and Jones Jr made major headlines with their exhibitionCredit: Joe Scarnici/Triller

9. Floyd Mayweather vs Tenshin Nasukawa (2018)

The strangest of Floyd’s growing list of exhibitions. First announced as some mysterious hybrid-combat contest, Floyd quickly made it clear he would not be fighting the unbeaten Japanese kickboxer in anything other than straight boxing rules over three rounds.

Predictably, the smaller, 20-year-old Nasukawa was battered around the ring by the former pound-for-pound king. ‘Money’ knocked down his foe three times in the first round and left poor Tenshin in floods of tears. “It was about entertainment and we had fun,” said Mayweather. Speak for yourself, Floyd!

Fair play, Shaq. The 7ft 1in NBA legend gave it his all when his ‘Shaq Vs’ series pitted him against a recently retired De La Hoya over five shortened rounds. While Oscar darted in and out, landing rapid combinations, O’Neal showboated – including an attempted Ali shuffle – and looped in body punches.

Shaq’s hulking 235lb frame helped (De La Hoya turned pro at a scrawny 130lb) but he stayed on his feet for a dignified points defeat. Enjoyed it so much he fought Shane Mosley in Las Vegas a year later with a similar outcome.

Nasukawa ended up on the canvas three times in quick succession

Nasukawa ended up on the canvas three times in quick successionCredit: Getty Images – Getty

7. Evander Holyfield vs Mitt Romney (2015)

If Vitor Belfort’s brutal KO of an aged Holyfield in 2021 was horrible to watch, this ‘fight’ six years earlier against a 68-year-old former presidential candidate was definitely stranger. We get the feeling the ‘Real Deal’ was pulling his punches against the unathletic politician.

Evander even took a staged tumble to the canvas before Romney’s corner threw in the towel in round two, perhaps fearing that Holyfield might suddenly forget where he was and start teeing off for real, giving Mitt an even worse defeat than Barack Obama handed him in 2012.

6. Dolph Lundgren vs Oleg Taktarov (2007)

Yes, mighty Ivan Drago actually had a full-contact boxing bout in Russia a mere 22 years after ‘Rocky IV’ came out. The towering Swede fought early UFC pioneer Taktarov at an event called King of the Ring in Moscow.

Lundgren had some boxing training and is a fourth-dan black belt in karate, so wasn’t a total novice. However at 47 years old (Taktarov was 39) it’s impressive that Dolph went the five-round distance with a man who’d battled the likes of Ken Shamrock, taking some flush punches to the chin but rumbling forward for a respectable points loss.

Holyfield hit the canvas against Romney

Holyfield hit the canvas against RomneyCredit: Getty

5. Sugar Ray Leonard vs Steve Sinclair (1982)

How did an all-time great end up fighting on a British cruise ship at the peak of his powers? Leonard, the unified welterweight champion, was a guest on the QE2. Sinclair was a waiter on the ship and ex-amateur boxer, so the two decided to entertain passengers with a cheeky five-round exhibition.

All fun and games until Steve got a bit excited and aimed some heavier blows at Sugar Ray’s recently surgically-repaired eye. So the champ upped the tempo and crunched in a few full-force body shots that left Sinclair gasping on the deck. “Every time I watch it, I feel it,” a proud Sinclair reflected later. “It was horrible!”

4. Muhammad Ali vs Antonio Inoki (1976)

The most iconic exhibition of all. Originally intended as a WWE-style staged bout in Tokyo, Ali got cold feet over engaging in a ‘fake’ fight. So organisers hastily put together some made-up rules: Ali had to box with gloves on; Japanese wrestling legend Inoki wasn’t allowed to grapple or takedown Ali.

A bizarre contest followed where Inoki crouched and aimed kicks at Ali’s legs, while the boxer tried to taunt his opponent into standing up to trade punches (Inoki wisely declined). Ali ended up with blood clots in his leg but the bout was declared a draw after 15 rounds. The crowd chanted: “Money back!” and threw rubbish into the ring.

Ali was not prepared for the onslaught Inoki gave his legs

Ali was not prepared for the onslaught Inoki gave his legsCredit: Associated Press

3. Trevor Berbick vs Nobuhiko Takada (1991)

Victim of Mike Tyson’s most devastating KO, ex-heavyweight champion Berbick engaged in an even stranger cross-combat bout than Ali-Inoki. Taking on pro-wrestling/MMA ace Takada in Japan, Berbick either thought it was a staged match – or simply had no idea what the rules were.

After the first bell, Takada swiped a hard low kick at Trevor and the baffled boxer complained bitterly to the referee. Takada kept on kicking, however, with Berbick’s protests to the official increasing. Eventually, the Jamaican simply stepped between the ropes and walked off into the crowd. Takada TKO1, we suppose.

2. George Foreman vs five men (1975)

Foreman, one of the most devastating heavyweight punchers ever, had lost his world title to one man (albeit that man was Muhammad Ali) in his previous bout. So what did promoter Don King arrange for his comeback? Foreman fighting five men in one night.

Big George promised ‘nothing but violence’ beforehand but seemed perplexed by boxing five journeymen, one after another. Caught between clowning around or trying to blast them out, Foreman did a bit of both. King dressed it up as an official event, but none of the five bouts ended up on the boxer and future grill millionaire’s record. Just weird.

In his prime, Foreman was a dominant champion who possessed one of the hardest punches in boxing

In his prime, Foreman was a dominant champion who possessed one of the hardest punches in boxingCredit: Getty

1. Tony Galento vs an octopus (1946)

Apparently they weren’t too concerned with animal welfare in the 1940s as colourful, cigar-chomping heavyweight contender ‘Two Ton Tony’ once boxed a kangaroo, a bear and – yes – a giant octopus called Oscar in a series of PR stunts.

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