Heavyweight boxing: The fights we missed out on in the 1990s, including Tyson vs Lewis

The heavyweight division in the 1990s was a beautiful era but as ever, there are always fights that fans wish could have happened.

The great boxing analyst Larry Merchant would often opine that boxing could be best described as the theatre of the unexpected. Capable of thrilling and frustrating in equal measure, the heavyweight fight game continues to encapsulate both of those rivalling emotions.

Today, two of the most prominent heavyweight champions of the past decade have yet to trade hands inside the ring - namely Tyson Fury and Anthony Joshua.

And so it has always been. Perhaps, no more so than the unforgettable period of heavyweight boxing during the 1990s.

Mike Tyson

An exceptional era that bore witness to Hall of Fame champions like Mike Tyson, Riddick Bowe, George ForemanEvander Holyfield and Lennox Lewis to name but five, the heavyweight scene during the final decade of the last century was a truly explosive and, at times, mesmerising period for the sport.

For better or for worse, the 1990s proved to be a truly golden era of heavyweight boxing.

Beyond those great champions I just mentioned, fighters like Michael Moorer, Andrew Golota, Tommy Morrison and Frank Bruno brought their own unique qualities and remarkable personal stories to the ring.

Yet despite all of the talent and personality on display, on so many occasions, the fights most craved by followers of the sport would somehow fall by the wayside. Either occurring too late or not at all, fight fans would be deprived of several potentially legendary bouts during an albeit brilliant era in heavyweight boxing.

Mike Tyson vs Evander Holyfield (1990-1991)

The 1990ss began with a then 23-year old Iron Mike Tyson very much ruling the division, having gobbled up the WBA, WBC, IBF, and The Ring heavyweight titles between 1986 and 1989.

Entering the new decade, Tyson, then 37-0 and still the destructive and most feared force in the division, was set to defend his unified titles in a hotly-anticipated bout against No.1 contender and former unified cruiserweight king Evander Holyfield in the summer of 1990.

All he had to do was first overcome the unheralded Buster Douglas in Tokyo, Japan. We all know what happened on that fabled Japanese morning.

Six months later, a remorseless Holyfield would snatch Douglas's freshly acquired crown with a straightforward and quick-fire KO of the one-fight wonder Buster. But, even then, the delayed showdown with a once-beaten but still revered Tyson still appeared to be on the horizon.

However, those hopes were again dashed with Iron Mike´s career thrown into doubt following his subsequent conviction for rape in early 1992. Tyson would serve three and a half years of a six-year sentence.

At 23 and 27, respectively, a bout between these two great heavyweights of the era would have been a fascinating occurrence had it first taken place in 1991. While they would, of course, share the ring twice in 1996 and 1997, a post-prison Tyson was no longer the brilliant and brutal force that had seen him clean out the division in the late 80s.

Having been stopped in the tenth round of their first bout, an out-of-control Tyson would famously lunch on Holyfield's ears in their subsequent rematch, earning the controversial Brooklyn native a third-round DQ and a year-long suspension from the sport.

While both bouts were undeniably unforgettable occasions, a 1991 fight between two then-unbeaten champions would have been a potentially even more absorbing and brilliant event with both men much closer to the peak of their powers at that time.

Of course, Holyfield remained a brilliant fighter when they did finally square off, even at 34. However, at 30, Tyson was some way removed from the explosive fighting tornado that had so absorbingly swept through the division prior to his incarceration.

Lennox Lewis vs Riddick Bowe

Lennox Lewis

The one that got away.

Lewis vs Bowe is surely the biggest fight of the era that failed to materialise in the professional ranks. While the two had met in the final of the 1988 Olympics (Lewis won by stoppage), a paid bout between these two giants of the division would remain one bout that will instead be forever debated.

In November of 1992, Evander Holyfield would defend his WBA, WBC, and IBF heavyweight titles against No1 challenger Riddick "Big Daddy" Bowe. Lewis, for his part, would come up against highly ranked contender Donovan "Razor" Ruddock.

The winner of that bout guaranteed a shot at the man to emerge from the Holyfield/Bowe contest with all three recognised heavyweight titles.

Lewis, at 27, while not yet the dominant figure that would rule the division later in the decade, scored a dominant second-round KO of the out-gunned Ruddock, who himself had gone the distance with Mike Tyson just 15 months earlier.

However, having claimed a brilliant win in a wonderful back and forth brawl with Holyfield in the first of their three legendary bouts, Bowe would instead, quite literally, bin his recently acquired WBC title rather than facing the then-unbeaten Brit.

Cowardice or not, the ill-disciplined Bowe, managed by madcap Rock Newman, had certainly talked a good game but rather than face Lewis, instead choosing to face fringe contenders Michael Dokes and Jesse Ferguson before losing his titles just 12 months later in the rematch with Evander Holyfield.

Three years later, Lewis and Bowe finally signed a contract to fight in Las Vegas in March of 1995. Lewis would first have to defend his WBC title against Oliver McCall in London. Remarkably, the unbeaten Brit would lose his title to the little known McCall, and the long-awaited Bowe/Lewis bout was shelved for a second occasion.

Sadly for fight fans, this battle of the big men would never come to fruition.

While Bowe edged a third bout with Holyfield, two infamous beat-downs from the no-nonsense Pole Andrew Golota sent Big Daddy into retirement at the age of 29 and with it, any lingering hopes that the two giants of the division would finally meet in the professional ranks had gone.

Lennox Lewis vs Mike Tyson

Ok, this one happened too. But far, far too late.

Arguably the biggest fight of the era, these two great heavyweights finally got it on in the summer of 2002. However, at ages 36 and 35, respectively, both men, particularly Tyson, were far removed from their prime when they finally shared a ring in the unfamiliar surroundings of Memphis, Tennessee.

Tyson, arguably at his peak between 1987 and 1990, had suffered back-to-back losses against Evander Holyfield five years prior to the long-awaited bout and looked a long way removed from his prime, even in subsequent victories against Frans Botha, Andrew Golota (later ruled a no-contest) and Brian Nielson between 1999 and 2001.

Still, that desire to see these two greats of the sport finally meet in the ring remained. With both approaching their 37th and 36th birthdays, only nostalgics and those with only a passing interest in the sport retained much hope that the fight would live up to the occasion.

And so it proved.

Lewis, while an ageing champion, remained very much the dominant force in the division. Too strong, too skilled and too cool, he was far too good for this version of Mike Tyson. A dominant beatdown preceded an eighth-round KO, with Lewis finally claiming the scalp of the last great rival of his era and, with it, the long-craved respect of an often underwhelmed fighting public.

While Lewis had undoubtedly risen to the top, and despite the similarity in age, these two great fighters enjoyed their respective peaks at very much different junctures in their careers.

In Memphis, Tyson was little more than a caricature of his once-great self. A ghost of the once Baddest Man on the Planet. Lewis, while probably a little past his best, retained enough of the force and dominance of his peak to end the Tyson myth.

Yet it might well have been different - certainly if they had fought some 10 years earlier. Even in 1996, a post-prison Tyson at 29 would have provided Lewis with a far stiffer examination of his skills. At 21, few would dispute the notion that Tyson would likely have had far too much for the great Brit to deal with.

Ifs and buts and maybes. Boxing is very much a Sliding Doors sport. A twist of fate or a fateful punch landed, the sport's history is written on those moments missed, as much as those moments experienced.

A brilliant, near unrivalled era of excitement, the 1990s produced a remarkable series of heavyweight fighters and fights engaging rivalries, inside and outside of the ring.

While it wasn't often perfect, drama and destruction, sometimes self-inflicted, it was very much the order of a wonderful era of heavyweight boxing.

Read more: Oleksandr Usyk - From undisputed cruiserweight ruler to heavyweight king

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