Great Matchups in Boxing History That Never Happened

As talk of Tyson Fury and Anthony Joshua meeting in the ring continues, we look at some of the greatest would-be boxing clashes that failed to materialise.

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There are few things in sport that rank as highly as boxing when it comes to getting the biggest names to step into the ring to fight each other.

Sugar Ray Robinson v Jake LaMotta, Muhammad Ali v Joe Frazier and Sugar Ray Leonard v Thomas Hearns are just three which lived up to the hype, while the biggest grossing fight of all time was Floyd Mayweather versus Manny Pacquiao in 2015 as the two legends finally danced together in the supposed fight of the century.

As it turned out, the fight did not match those expectations with Mayweather comfortably winning by a unanimous points decision.

That fight showed the reality doesn’t always match the fanfare, but it remains disappointing when a deal cannot be done. 

Tyson Fury and Anthony Joshua supposedly had a contract sealed for a two-fight contract to get it on in the summer of 2021 and then a rematch in what would have been the biggest fight in British boxing history.

With the fight now looking further away than ever before it could mean Fury and Joshua never let their fists do the talking and here’s five other occasions when fans were left frustrated.

Mike Tyson v George Foreman

It would have been a clash of the titans and a meeting of the heavyweight eras and, despite many rumours of a signed contract, Tyson versus Foreman was never to be.

Foreman, who became world heavyweight champion in 1973 thanks to a stunning win over the previously undefeated Joe Frazier, was involved in one of the all-time great fights in 1974 when he lost to Muhammed Ali in the Rumble in the Jungle.

Big George retired from the ring in 1977, only to return a decade later and in 1990 it seemed certain Foreman would face the dominant Tyson following an impressive win over Gerry Cooney. 

However, Tyson was shocked by James “Buster” Douglas less than two months later and Iron Mike was serving a prison sentence when Foreman, at 46, became the oldest world heavyweight champion in history after beating Michael Moorer.  

Riddick Bowe v Lennox Lewis

Tyson also missed out on fighting Riddick Bowe during his time in prison, but more frustrating was Big Daddy and Lennox Lewis avoiding each other in the pro ranks.

Lewis beat Bowe in the 1988 Olympics final but with a rematch set for 1993 the American dumped his WBC belt in the trash bin rather than take the mandatory fight.

There was always talk that the pair would fight again, but to no avail.

Sugar Ray Leonard v Aaron Pryor

It is a fight that has been discussed in pubs and clubs across the world – would Aaron Pryor have beaten Sugar Ray Leonard?

Pryor and Leonard both went to the 1976 Olympics, Pryor dropping down a weight to accommodate both on the same team, but when a fight seemed likely Sugar was forced to retire as an undisputed champion following a serious eye injury aged 30. 

Floyd Mayweather v Paul Williams

Money man Floyd Mayweather would always enjoy a large purse – he even fought MMA’s Conor McGregor in a one-sided farce – but annoyingly he missed out on Antonio Margarito and Kostya Tszyu and there was a much sadder story to a potential fight with Paul Williams.

The Punisher defeated Margarito but was left paralysed from the waist down following a motorbike crash in 2012.

Roy Jones v Chris Eubank

Both had titles at middleweight and super-middleweight but never met to unify the belts and Chris Eubank very honestly said: “My view was Roy, I will admire you from afar!”

The legendary Jones now trains Eubank’s son, Chris Jr, but for many older fans they would have loved to have seen Eubank senior take on one of the best ever.

An experienced sports journalist, Henry’s knowledge spans across a number of different areas, including darts and snooker.
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