On Friday, Anthony Joshua returns to the ring for a surprise fight against YouTube star Jake Paul. Below, we look back at some of the most unusual matches in boxing history…
George Foreman vs Five Men
After his stunning loss to Muhammad Ali, George Foreman’s fearsome reputation took a total hit. That was something he was having a hard time dealing with. What is the answer to restoring his honor? One afternoon in April 1975, he wrestled with five men.
Don King’s promotion was billed as “the premier boxing exhibition spectacle” and Ali participated in the correspondence. This was generally seen as more of a publicity stunt than a legitimate challenge.
Foreman won all five bouts, but the first three were by stoppage. Eventually fatigue set in and the showboating began, but the spectacle cemented the event into boxing folklore.
Muhammad Ali vs Antonio Inoki
Muhammad Ali participated in a huge number of exhibition matches throughout his career, but his match against Antonio Inoki in Tokyo in 1976 was particularly memorable.
Inoki, a star in the Japanese wrestling world, was limited by regulations that prohibited standing takedowns, submissions, throws, and kicks.
As a result, Inoki immediately fell onto his back in the first round and began repeatedly kicking Ali. Inoki threw over 100 kicks, but Ali could barely land any punches. Inoki was praised for surviving, but Ali was left with a mangled leg. It was strange, farcical, and somehow ended in a draw.
Trevor Berbick vs Nobuhiko Takada
In another event that was literally advertised as “Boxers vs. Wrestlers,” former heavyweight world champion traveled to Japan in 1991 to face Nobuhiko Takada.
Berbick was unaware that Takada could kick below the belt. What happened next was mostly slapstick. As Takada continued to kick, Berbick protested repeatedly to the referee.
Berbick left the ring without throwing a punch, feeling frustrated and humiliated.
Oscar De La Hoya vs Shaq O’Neal
One of the most memorable matches on the list took place in 2009 as part of a television series. NBA star Shaquille O’Neal donned headgear and faced off against Oscar De La Hoya in four two-minute rounds.
De La Hoya was declared the winner by unofficial unanimous decision. Both this match and the series received widespread criticism.
Evander Holyfield vs Mitt Romney
In 2015, 68-year-old former Republican presidential candidate Mitt Romney stepped into the ring with 52-year-old Evander Holyfield.
Romy quipped: “The good news is that Evander Holyfield always hits more than Belt, but sometimes that’s not the case in politics.”
Holyfield fell to the mat early in the fight, and Romney threw in the towel after two rounds. The good thing about this match? We raised money for charity.
Floyd Mayweather vs Conor McGregor
Even Jake Paul will have a hard time matching the financial success of the Mayweather vs. McGregor fight in 2017, which raised about $600 million. Could a non-professional beat one of boxing’s greats in his sport? Naturally, the answer was no.
McGregor got off to a decent start, showing some sharpness in the early rounds, but it quickly became clear that his mixed martial arts striking power wouldn’t translate to boxing. Mayweather toyed with him and eventually stopped him late in the fight.
While the result wasn’t all that shocking considering Mayweather’s perfect 49-0 record, it still seemed shocking to some MMA fans.
A match between Paul and Joshua may raise some eyebrows, but it’s far less ridiculous than some of the historical oddities we’ve seen so far. And that’s the point to remember: Boxing, for all its seriousness and skill, has never been able to avoid theatrical chaos.




