Boxing’s Biggest Fights That Never Happened

Many illustrious fights have stood the test of time. When two greats meet in the ring they become a part of boxing history.

But the greatest match-ups haven’t always materialised throughout various decades of the sport.

Despite top names sharing divisions or two legends competing in the same era, sometimes they frustratingly never met in the ring.

As the long-awaited undisputed welterweight showdown between Errol Spence Jr. and Terence Crawford hits a stumbling block for now, here’s a look back at the biggest boxing fights that never happened.

Boxing’s Biggest Fights That Never Happened

1. Mike Tyson vs George Foreman
2. Sugar Ray Leonard vs Aaron Pryor
3. Roberto Duran vs Alexis Arguello
4. Jack Dempsey vs Harry Greb
5. Floyd Mayweather Jr. vs Paul Williams
6. Lennox Lewis vs Riddick Bowe
7. Juan Manuel Marquez vs Erik Morales
8. James Toney vs Chris Eubank Sr.
9. Sugar Ray Robinson vs Charley Burley
10. Miguel Cotto vs Ricky Hatton
11. Other notable missed fights

1. Mike Tyson vs George Foreman

Tyson vs Foreman is one of the biggest boxing fights that never happened (Photo credit: WBC).

The names of heavyweight greats Mike Tyson and George Foreman often come up in talks of a fantasy fight but the two former champions were once close to meeting in the ring for real.

In the early 1990s, Tyson entered a career-altering period in his life, as he suffered a monumental upset at the hands of Buster Douglas before his eventual three-year prison stint.

While ‘Iron Mike’ was rebuilding himself from the Douglas defeat, Foreman had re-entered the picture on his incredible return and was touted as a potential comeback opponent for Tyson.

Instead, he knocked fought and beat Henry Tillman, Alex Stewart and Razor Ruddock before being jailed, as Foreman went on to push then champion Evander Holyfield in a defiant decision defeat.

This showdown of legends was again on the cards when Tyson was released in 1995 and Foreman had remarkably become the oldest world heavyweight champion in history.

But Tyson, now a lesser fighter to that who rampaged through the division during his initial reign, was re-establishing himself before his second title victory and a Foreman match-up frustratingly never materialised.

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2. Sugar Ray Leonard vs Aaron Pryor

Sugar Ray Leonard was close to facing off with Aaron Pryor (Photo credit: @SugarRayLeonard on Twitter).

One of boxing’s biggest near-misses between two legendary champions of their era. Sugar Ray Leonard, one of the greatest fighters in history, came very close to facing the destructive Aaron Pryor.

Pryor’s light-welterweight career coincided with Leonard, Roberto Duran and Tommy Hearns, who were all competing at 147 pounds, but he was unable to ever get any of those illustrious names in the ring with him.

The showdown with Leonard was close to fruition though, after unsuccessful financial negotiations were eventually overcome and an agreement was made for a welterweight title fight in 1982.

But ‘The Hawk’ never got his shot at Leonard, who suffered a detached retina during a tune-up fight and subsequently retired for the first of many times throughout his career.

Pryor instead went on to face the great Alexis Arguello that year, earning a famous 14th-round knockout, before a quick-fire first-round stoppage in their rematch the following year.

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3. Roberto Duran vs Alexis Arguello

Duran and Arguello are two all-time greats of the sport (Photo credit: Panama America).

If the fights between Roberto Duran-Sugar Ray Leonard and Aaron Pryor-Alexis Arguello were anything to go by, a possible clash between ‘Hands of Stone’ and ‘The Explosive Thin Man’ would have produced fireworks.

Arguello had moved up to fight at lightweight, after title victories at featherweight and super-featherweight, and a blockbuster meeting with Duran was in talks before the end of the 1970s.

But Duran was busy wrapping up his devastating run through the lightweight division, where he’s widely regarded as the best fighter ever at 135 pounds, and he would crazily end up at middleweight in the 1980s.

It’s another mouth-watering fight between two iconic greats that sadly never happened but one that leaves boxing fans wondering, what if?

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4. Jack Dempsey vs Harry Greb

A fight between Dempsey and Greb would have been historic (Photo credit: Bill Paxton).

Looking back to the ‘Roaring Twenties’ at an almost-agreed fight that could’ve changed the course of boxing history and had a lasting impact on the sport.

Jack Dempsey was a cultural icon of his era, reigning as heavyweight world champion from 1919 to 1926 and becoming one of the first major superstars of the sport.

Paralleling the rampant run of ‘The Manassa Mauler’ was an equally savage middleweight by the name of Harry Greb, who incredibly went 45-0 in 1919 alone (a feat that never has and never will be emulated).

‘The Pittsburgh Windmill’ is regarded by historians as the greatest prize-fighter ever due to his exceptional resume, which includes 298 fights across a 13-year career and began at welterweight but saw him face off with light-heavyweights and heavyweights.

One heavyweight Greb never got to challenge was Dempsey, who he is reported to have got the better of in regular sparring sessions at the height of his powers.

Newspaper cuttings from 1920 stated: "Greb was all over him and kept forcing him around the ring throughout the session. Greb seemed to be able to hit Dempsey almost at will."

Later that same year, talks of a proper fight between the popular pair surfaced but failed to confirm anything as Dempsey instead defended his crown against Bill Brennan.

In 1922, Dempsey outlined intentions of making the fight again, saying: "It is possible that I might get a match with Harry Greb."

It never happened, sadly. Dempsey was inactive that year with no fights, while Greb had 12 bouts and handed future Dempsey conqueror Gene Tunney his first and only career defeat.

Dempsey-Greb would have been one of the biggest fights of all-time for its time period. The fact that no known fight footage of Greb exists adds further frustration to the failed match-up, as a clash with Dempsey would have no doubt been recorded and been widely watched to this day.

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5. Floyd Mayweather Jr. vs Paul Williams

Mayweather retired before the chance of a Williams fight taking place (Photo credit: Al Bello/Getty Images).

There’s no denying Floyd Mayweather Jr’s credentials as an all-time great, having retired with a 50-0 record and facing many of the best fighters throughout his career.

Especially on his way up through the lower weights, ‘Pretty Boy’ overcame experienced champions to see his reputation rocket and put himself into prime position as a superstar later as he moved up divisions.

But, after defeating Oscar De La Hoya and rising to superstardom, Mayweather became known for using his A-side status to his advantage.

This paved the way for many fans to argue he ‘ducked’ some potential challengers to his throne, most notably delaying clashes with Manny Pacquiao and Shane Mosley until late in their respective careers.

Paul Williams was one other such name. The towering six-foot-one southpaw was an intimidating welterweight champion with a 79-inch reach and was a possibly nightmare foe for ‘Money’ Mayweather’.

In 2007, Williams dethroned Antonio Margarito as 147 pounds champion and Mayweather edged out De La Hoya then dispatched Ricky Hatton, leaving the showdown as a promising option.

But Mayweather opted to retire from the sport, with his time away eventually ending after two years, while Williams moved up divisions in 2008 and was tragically paralyzed from a motorcycle accident in 2012.

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6. Lennox Lewis vs Riddick Bowe

Lewis and Bowe met in the amateurs but never as professionals (Photo credit: Getty).

Lennox Lewis overcame Riddick Bowe in the 1988 Olympic Gold medal fight for Canada as amateurs but a professional clash between the pair is one of the biggest boxing fights that never happened from the 1990s.

‘Big Daddy’ was first to win a world title in the paid ranks, as he conquered Evander Holyfield in 1992 to reign as heavyweight champion.

Lewis was a rumoured opponent in light of the Bowe’s title victory and, with a ready-made storyline from their amateur past hyping the fight up, it looked set to occur.

But it didn’t. Lewis went on to beat Tony Tucker in 1993 to become champion himself, with a Bowe showdown later mooted again midway through the decade.

The stunning upset suffered by Lewis at the hands of Oliver McCall unfortunately derailed the highly-awaited meeting again in 1994.

Then in 1996 the anticipated showdown was buried for good when Bowe decided to walk away from the sport after back-to-back disqualification defeats to Andrew Golota. One of the major fights that sadly got away.

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7. Juan Manuel Marquez vs Erik Morales

Marquez never got to fight fellow Mexican legend Morales (Photo credit: Chris Farina/Top Rank).

It’s almost hard to fathom that Mexican greats Juan Manuel Marquez and Erik Morales never came to blows in the ring, despite competing in the same era for so long.

A round-robin of epic match-ups between the pair and Marco Antonio Barrera and Manny Pacquiao produced 13 memorable fights between 2000 and 1012.

But Marquez-Morales was a key absence, in spite of them battling in and around similar divisions for around a decade.

An all-Mexican affair would’ve made for a blockbuster but 2011 negotiations sadly never produced anything solid.

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8. James Toney vs Chris Eubank Sr.

Toney called out both Eubank Sr. and Benn in his career (Photo credit: Al Bello /Allsport)

Never one to shy away from calling out fighters in his prime, regardless of weight classes, James Toney was ready and willing to face-off against an equally eccentric Chris Eubank Sr.

Ahead of Eubank’s iconic battle with Nigel Benn in 1993, Toney called out both British rivals live on TV in typically brash fashion.

“I don’t care who wins and I’ll fight either one of them. I’ll fight both of them on the same night. When I see you, imma beat you and your momma’s ass,” declared Toney.

A draw between Eubank and Benn in Manchester seemed to scupper any immediate chances of either then taking on the formidable Toney.

But ‘Lights Out’ went on to suffer a maiden career loss to Roy Jones Jr. and lose his super-middleweight title before beginning his move up the divisions, ending hopes of any America vs England clashes.

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9. Sugar Ray Robinson vs Charley Burley

Robinson is known as the GOAT but never faced off with the avoided Burley (Photo credit: Bert Hardy/Getty Images).

A fighter in a class of his own, Sugar Ray Robinson is widely known as the greatest boxer in history with a record of 174 career wins including 109 knockouts.

Robinson faced the best of his generation but there were instances when even the GOAT was accused of steering clear of dangerous rivals.

Charley Burley was one of those men. Part of boxing’s ‘Black Murderer’s Row’, he was denied a world title shot throughout his career due to the colour line being drawn against him.

Burley was forced to go into tougher match-ups against fellow black contenders as a result and eventually ended up taking on heavyweights.

George Gainsford, the manager of welterweight and middleweight champion Robinson, even later admitted he kept his fighter away from Burley during his title reign.

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10. Miguel Cotto vs Ricky Hatton

Cotto vs Hatton is one of biggest boxing fights that never happened (Photo credit: Mike Ehrmann/Getty Images).

In what could have been a modern-day classic, multiple weight world champions Miguel Cotto and Ricky Hatton unfortunately never got to collide in the ring.

In the same weight classes and competing in the same era, it’s another big miss for boxing fans for what would have likely been a great gelling of styles.

Both men faced off with other greats of their era, such as Manny Pacquiao and Floyd Mayweather Jr, leaving the door open for a potential showdown.

There were hints of the bout taking place from 2006 to 2009 but unfortunately it never came to fruition.

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11. Other notable missed fights

Gonzalez and Inoue are two great smaller division fighters but never crossed paths (Photo credit: KAZ NAGATSUKA).

1. Sergio Martinez vs Gennadiy Golovkin

2. Shane Mosley vs Felix Trinidad

3. Joe Frazier vs Ken Norton

4. George Foreman vs Earnie Shavers

5. Riddick Bowe vs Mike Tyson

6. Sergey Kovalev vs Adonis Stevenson

7. Roman Gonzalez vs Naoya Inoue

8. Evander Holyfield vs Vitali Klitschko

9. Floyd Mayweather Jr. vs Antonio Margarito

10. Prince Naseem Hamed vs Juan Manuel Marquez

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Header image credit: Bettmann