Back in June, Andy Ruiz Jnr dropped Anthony Joshua four times on the way to scoring a dramatic seventh round knockout and one of the great heavyweight boxing upsets of recent times. But the history of the fight game is littered with shock results which no-one - or only very few - saw coming.

So we’re taking a look back at five other heavyweight upsets from the past, counting down in “shock factor” from five to one. AJ is in fine company, with Lennox Lewis, Mike Tyson and Muhammad Ali - as the young Cassius Clay - all featuring. But first, we’re starting off with some more recent boxing history…

#5: Wladimir Klitschko v Tyson Fury | November 28th 2015 | Dusseldorf, Germany

A 6’9” fighting traveller named Tyson Fury was always likely to make headlines, one way or another. But even in the chaotic and colourful history of the fight game, few journeys can match for sheer improbability that trodden by Manchester’s self-styled ‘Gypsy King’.

Leaving school before his teens with no qualifications, Fury soon found boxing and despite his awkward, gangling frame, discovered he was a natural. Perhaps that’s no great surprise for a man born into a travelling community whose extended family includes the feared, notorious bare-knuckle boxing champions Uriah Burton and Bartley Gorman.

After winning several amateur titles, including super heavyweight gold at the 2008 English National Championships, Fury turned pro later that year. Scoring a 1st round KO on debut, the Gypsy King was on his way.

Ukraine’s Wladimir Klitschko meanwhile, 12 years Fury’s senior, was by this time a veteran of 54 professional contests and held three versions of the world heavyweight title. Stepping out from the not inconsiderable shadow of his older brother Vitali, and under the tutelage of legendary trainer Emmanuel Steward, Wladimir had overcome a couple of early setbacks and developed into a fine world champion.

Derided in some quarters as a one-dimensional automaton, the sage-like Steward maintained that Klitschko had all the tools necessary to go down as one of boxing’s very best. Certainly that pulverising right-hand was a terrifying weapon, the mere threat of it enough to dissuade David Haye from showing any aggressive intent in his hugely anticlimactic bid for Klitschko’s titles in 2011.

Two years later, Fury himself was set to cross paths with Haye, but two scheduled bouts never came to pass, the ‘Hayemaker’ citing injury and pulling out of both. That period of on-again off-again inactivity with Haye cost Fury his own place in the pecking order for a crack at Klitschko’s crown.

Regarded as one to watch from his early days – not that he was easily missed – Fury was considered an accomplished if eccentric talent, but it was by no means certain he would make it to the top. He was floored in his 13th contest, and rather unkindly labelled as a bit of a lummox for having memorably punched himself in the face in another early outing.

Nevertheless, he was 24-0 by the time he entered the ring against Klitschko, with two victories over a roughhousing Derek Chisora (one on points, one stoppage) his career highlights to date. ‘Dr. Steelhammer’ although by now 39 years old, entered the ring with a professional record of 64-3, with 53 knockouts, and hadn’t been beaten for over 11 years.

Even by the standards of professional boxing, Fury’s performances in the pre-fight press conferences were something to behold. Despite’s Klitschko’s best attempts to keep things civil (boring, according to Fury), the Gypsy King was having none of it, infamously turning up to one of them dressed as batman, because, well, Tyson Fury.

A natural showman, Fury provoked the polished, respectful champion who was taken aback by Fury’s antics and insults. The barely disguised contempt in which Klitschko held the challenger was plain for all to see.

Come fight night, yet more drama was to unfold before the first bell had even sounded. The Klitschko camp, on ‘home’ territory in Germany, started playing mind games in an attempt to unsettle Fury and show everyone who was in charge.

After the Klitschko camp reneged on previously agreed stipulations regarding gloves and ring size, a livid – ok, furious – Team Fury threatened to pull out of the fight with the arena already filling up. They refused to back down. Fury had made his point and the fight was on.

Facing one of the most formidable champions in history, away from home and in front of a 55,000 sell-out crowd, most hoping for and expecting an easy Klitschko win, Fury was showboating less than 90 seconds in. Throwing feints and snapping out jabs with the champion in pursuit, Fury won the first, gave Klitschko a mouthful at the bell and walked back to his corner, arms aloft.

The pro-Klitschko crowd voiced their disapproval at such audacity, but there was a point to it. Fury was showing he could handle the occasion and the pattern of the fight had been set. Jabbing from the hip, switching stance, using his height and reach effectively, Fury succeeded in unsettling the champion who couldn’t do much more than paw tentatively for an opening which never came.

Fury was executing his game plan perfectly, bamboozling Klitschko, despite the ever-present threat of the champion’s concussive big right hand, held cocked and ready throughout. Although the challenger appeared to be in complete control, Klitschko hadn’t been seriously hurt and there was still the nagging doubt about how the judges might be scoring it.

In the ninth round, Klitschko finally let the right hand go but Fury took it well and responded with a left-hook of his own as the champion failed to press on. Then in the eleventh, more drama as Fury finally managed to rock the increasingly ragged Klitschko, before being docked a point for consistent blows to the back of the head. Both fighters came out swinging in the last looking to finish strong, and the outcome was left to the judges.

Most ringside observers had Fury ahead, and in the event the judges agreed, with the challenger winning by unanimous decision. In true traveller tradition, the new champion celebrated with a song, serenading his wife in the ring. Of even greater surprise to the still stunned crowd was the fact that he was actually pretty good.

From campsite caravan to the heavyweight championship of the world. The Gypsy King could now lay claim to the prized ‘lineal’ title held by boxing royalty from Lennox Lewis, Mike Tyson, Muhammad Ali, Rocky Marciano, Joe Louis, Jack Dempsey and Jack Johnson, all the way back to John L. Sullivan.

As is so often the case in boxing, the pre-fight nonsense gave way to a mutual and genuine respect after the fight. Ultimately, Fury was a puzzle that Klitschko couldn’t solve and the great champion, ever gracious, acknowledged as much. Fury for his part, apologised to his vanquished foe. A rematch was agreed, but never took place. Soon after Dusseldorf, Fury’s well publicised mental health battles began.

Klitschko instead turned his attention to Anthony Joshua, flooring AJ in the sixth before succumbing to an eleventh-round stoppage in front of 90,000 fans at Wembley. Aged 41 and with no more challenges left to face, Klitschko wisely called it a day.

As for Fury, his story has many chapters as yet unwritten. As it turned out, that night in Germany was just the end of the beginning, not the beginning of the end.

Perhaps the last word should go to the late, great trainer of champions, Emmanuel Steward. Years before they fought, Steward had called Fury “the next dominant heavyweight champion” and “the heir to Klitschko’s throne”. On pugilistic matters, Detroit’s wise old man of boxing rarely got it wrong.

#4: Lennox Lewis v Hasim Rahman | April 22nd 2001 | Brakpan, South Africa

The great Lennox Lewis, pugilist specialist, was twice sent sprawling to the canvas in devastating, unexpected knockout defeats. Both losses were later avenged, which did not of course diminish the shock of either upset at the time.

His first fight against Hasim Rahman was the classic cautionary tale of an over-confident, complacent champion underestimating a fired-up challenger who knew he was getting his one big shot - and grabbed it with both hands. Or more accurately, with one huge right hand.

By 2001, Lewis reigned supreme as the heavyweight division’s dominant fighter. His only serious rival to that claim was Evander Holyfield, whom he beaten by unanimous decision 18 months earlier after first fighting the ‘Real Deal’ to a controversial draw.

Over the previous decade, Lewis had dispatched a string of 90s notables including Holyfield, Michael Grant, Shannon Briggs, Andrew Golota, Henry Akinwande and Ray Mercer. He’d stopped Frank Bruno in seven rounds in 1993, shortly after announcing his arrival as a top tier heavyweight with a stunning two-round demolition of the dynamite-fisted Donovan ‘Razor’ Ruddock.

The heavy-hitting Ruddock had given a peak Mike Tyson all the trouble he could handle in two thunderous bouts, but Lewis just blasted him away. His lone defeat to Oliver McCall – more on that later – had been avenged in some style, and he was unbeaten in seven years entering the ring against the respected but unheralded Hasim Rahman from Baltimore.

The names on Rahman’s CV were no match for Lewis’s. Corrie Sanders – who would go on to knockout Wladimir Klitschko in another big upset – had been stopped in seven, but Rahman had lost against both Oleg Maskaev and David Tua. Lewis had beaten Tua easily in his fight prior to Rahman.

A glance at the two fighters’ amateur record summed up the different levels they were operating on. Lewis was a standout star, defeating future world champion Riddick Bowe to land super heavyweight gold at the 1988 Seoul Olympics. Rahman had fought only 10 amateur bouts, first lacing up a pair of gloves aged 20 in an attempt to escape the Baltimore street life which had nearly killed him on several occasions.

And yet, the warning signs were there.

The fight was being staged at Carnival City, a short drive from Johannesburg, South Africa at an altitude of nearly 6,000 feet. To accommodate US TV networks, it was scheduled to begin at 5am local time.

Lewis had trained, poorly by most accounts, in Los Angeles, arriving in South Africa less than two weeks before the fight. His arrival was delayed due to being on set for a cameo role in the Hollywood blockbuster Ocean’s Eleven, featuring an all-star cast including George Clooney, Brad Pitt and Julia Roberts.

Pre-fight talk centred on a lucrative showdown against Mike Tyson, a fading force at 35, after Lewis had taken care of Rahman. When the champ tipped the scales at a career high 18st 1lb, the impression was not one of a focused heavyweight champion with his mind on the job.

The chance to fight for the world heavyweight title was probably not something the young Hasim Rahman thought about much while he was getting shot and stabbed growing up in Baltimore. He’d also survived a fatal car accident, at a price of 500 stiches to his face and neck.

But ever since finding sanctuary in the boxing gym, he was totally dedicated to the sport, and he sensed that Lewis was taking him lightly. Rahman based his training camp in New York’s Catskill Mountains to prepare for the altitude, and arrived a month before the fight to acclimatise further. In short, he was preparing like a champion.

Billed as ‘Thunder in Africa ’, at stake were Lewis’s WBC & IBF heavyweight titles. Both men looked calm as they entered the ring, Lewis relaxed as always, Rahman confident.

They each enjoyed reasonable success early on, but it was Lewis who led 39-37 (three rounds to one) on all three judges’ scorecards after four rounds. But the champion was looking laboured, breathing heavily on his stool between the fourth and fifth.

Certainly, Rahman was in the contest and didn’t look like the 20/1 outsider the bookies had made him. He had some swelling around his left eye after an accidental clash of heads, but all that was about to prove irrelevant.

Lewis started the fifth well but was tagged by a solid Rahman right in the second minute of the round. The challenger followed up with a series of jabs, none of which seemed to trouble the champion as he leant back off the ropes, smirking.

But he wasn’t smirking for long as Rahman came again and detonated a huge straight right, landing flush on the champion’s jaw with 40 seconds to go in round five. Lewis was dropped heavily and wasn’t even close to beating the count. For the second time in his career, he’d suffered a stunning upset knockout defeat.

The outcome is often put down to Lewis’ lack of preparation, but that does a disservice to Rahman. Lewis’s trainer Emmanuel Steward claimed that it wasn’t lack of fitness but more a lack of “mental focus and intensity”, and the boxing ring is the wrong place to be doing without either of those.

“I would have expected Lennox Lewis to win that fight seven days a week, 24 hours a day”, exclaimed George Foreman, as the dazed, dethroned Lewis was left asking his corner, “what happened?”.

It seemed strange that Lewis, a consummate professional and one of the smartest fighters in the game, would fall into the trap of under-estimating his opponent – especially as he’d already done similar with such dire consequences earlier in his career.

The fall out was unseemly, Lewis claiming that Rahman got lucky, Rahman demanding his respect. With Rahman joining Don King after becoming champ, Lewis had to go through the courts to get his contractually obliged rematch.

Seven months later in Vegas, a much sharper Lewis delivered emphatically. Landing a massive right hand every bit as devastating as Rahman’s in the first fight, it was all over in four rounds. Lewis had his belts back.

A sore loser after the first fight, Lewis wasn’t exactly a gracious winner second time round. That was out of character for one of boxing’s more thoughtful and level-headed champions.

It just goes to demonstrate the extreme mental and physical demands that boxing at this level places on its combatants. But Rahman, a decent man despite his wayward past, deserved better treatment from Lewis. It ended 1-1 between them, after all.

By now 36 years old, Lennox Lewis, self-proclaimed ‘pugilist-specialist’ and one of Britain’s greatest ever, was approaching the end of the line. After two more wins over Mike Tyson and Vitali Klitschko, the big man was done.

Hasim Rahman, still in his twenties, would go on to have another 24 contests, eventually calling it quits at the age of 41.

But those two fights with Lewis set him up for life. Still in the game as a mentor to young boxers, it turned out to be a happy ending for the man from Baltimore - a man who came from nowhere to claim the heavyweight championship of the world, and his place in boxing folklore.

#3: Lennox Lewis v Oliver McCall | September 24th 1994 | London, UK

Long before his catastrophe against Hasim Rahman in South Africa, Lennox Lewis had to endure another nightmare against a maverick puncher from Chicago named Oliver McCall.

To describe McCall as a volatile character would be playing it down, and then some. He had a long history of substance abuse, would often make his way to the ring in tears, and his bizarre moniker the ‘Atomic Bull’ was entirely apt.

In the post-Mike Tyson heavyweight landscape, a trio of outstanding fighters emerged to stake their claim as top dog in the division following Tyson’s incarceration in 1992: Lennox Lewis, Evander Holyfield and Riddick Bowe.

Holyfield had made short work of Tyson-conqueror James ‘Buster’ Douglas in 1990, but lost his undisputed title two years later in the first fight of a classic trilogy against the exceptional Bowe, a former classmate of Tyson from Brownsville, Brooklyn.

Bowe had lost to Lewis in the super-heavyweight final of the 1988 Seoul Olympics, and their rivalry grew more bitter as they made their way through the paid ranks. In late 1992, just two weeks after Bowe’s defeat of Holyfield, Lewis faced off against the hard-hitting Canadian Donovan ‘Razor’ Ruddock in a final eliminator to challenge for Bowe’s undisputed title.

Lennox delivered perhaps his finest ever performance in a ruthless two-round destruction of the fearsome Ruddock, and Lewis v Bowe was on. Or was it? Rather than face Lewis, and with a chance to gain revenge for his Olympics defeat, Bowe refused the fight.

The WBC promptly stripped him of their title. Bowe’s response? To literally throw his WBC belt in the bin. It was an act of extreme petulance and a cheap PR stunt devised by Bowe’s controversial promoter, Rock Newman.

Awarded the WBC belt by default, Lewis made three successful title defences – the second of which was a seventh-round stoppage of Frank Bruno – before facing McCall at the Wembley Arena.

Lewis, holding an unblemished record of 25-0, was the overwhelming favourite. McCall, a former Tyson sparring partner and under the guidance of future Lewis trainer Manny Steward, had five defeats on his record but was still considered a dangerous, unpredictable fighter.

That assessment was proved absolutely correct. Just 20 seconds into round two, the Atomic Bull connected with an overhand right which sent Lewis crashing to the canvas for the first time in his career. He clambered gamely to his feet, but still clearly dazed, the referee stopped the fight. Lewis, arms outstretched in protest, had suffered his first pro defeat and McCall had pulled off a huge upset win.

The McCall camp celebrated wildly, no-one more so than promoter Don King - in full cackling maniac mode - cavorting around the ring, ecstatic to be back as a major player in the heavyweight division.

McCall made one successful defence of his title before returning to London a year later, losing on points as big Frank Bruno finally realised his world heavyweight dream on a memorable night at Wembley Stadium. Bruno’s dream quickly turned sour, as he was brutally stopped in three by Mike Tyson in his first title defence.

Lennox Lewis, now under the tutelage of Manny Steward – the man who masterminded his defeat to McCall – rebuilt steadily with four straight wins before facing McCall again in 1997. Things got weird in the rematch. McCall’s chaotic personal life had once more spiralled out of control. Inactive for almost a year, he went directly from rehab to training camp.

On fight night itself, he literally ran into the ring - as if desperate to get it over with - and tried for a couple of rounds before appearing to decide that he didn’t want to fight.

From the third round on, and to the bewilderment of spectators, commentators and Lewis alike, McCall refused to throw any punches or even try to defend himself. Referee Mills Lane had no choice but to call a halt less than a minute into the fifth.

Veteran US announcer Larry Merchant surmised, “I’ve seen some strange things in boxing. That is surely one of the strangest”. The Lewis camp knew they’d just witnessed a man having a very public breakdown, and to their credit, the celebrations were subdued.

Lewis would also avenge his only other defeat to Hasim Rahman, and can thus proudly claim that he beat every man he ever fought. Against all the odds, McCall, now 54, fights on, holding a record of 59 wins and 14 losses. His only defeat inside the distance remains that bizarre rematch against Lewis in Las Vegas.

What is a man still doing fighting at 54 you might ask? For the Atomic Bull, it seems like the ring is the safest place to be.

#2: Sonny Liston v Cassius Clay | February 25th, 1964 | Miami, USA

In 1964, the world – or America at any rate – was not yet ready for Cassius Marcellus Clay.

The man who would go on to achieve sporting immortality, and, as Muhammad Ali, become one of the most famous people of all time, was at this time simply a fleet-footed, fast-talking, precociously talented 22-year-old boxer.

Ali would of course go on to become, in his own words, “The Greatest”, and one of the most iconic figures of the 20th century, gaining a cultural significance beyond that of any mere sportsman. But all that lay a long way away when Clay, as he then was, made his first challenge for the world heavyweight championship.

Many ring observers felt he was in for - and frankly, hoped he would receive - a painful beating at the hands of the frighteningly powerful and downright terrifying champion, Charles “Sonny” Liston. The brooding, sullen Liston was everything the effervescent Clay was not.

Born into abject poverty, the second youngest of 25 children on farm in rural Arkansas, confusion has long surrounded Liston’s exact date of birth. Most accounts put it at either 1930 or 1932, but it’s likely earlier than that.

He endured a violent, miserable childhood, before running away from home aged 13, unable to read or write. He would eventually serve jail time for robbery, and it was in prison where he first began to box. Liston would later say that the food in the Missouri State Penitentiary was the best he ever ate.

Upon leaving jail in 1952, Liston embarked on a brief but successful amateur career before going pro under the management of the mafia, who effectively controlled US boxing in the post-war era. Liston’s criminal background and mob ties led to repeated run-ins with the law. He swapped St. Louis for Philadelphia but only found more trouble, and more serious underworld figures who took an interest in his career.

Despite this chaotic existence, by 1962 Sonny Liston had risen to #1 contender for Floyd Patterson’s heavyweight title. The two men could not have presented a more different public image.

The amiable Patterson was much-admired, and seen as the acceptable face of the civil rights movement. He had the support of community leaders, the public at large and even President John F. Kennedy wanted him to win. Nobody wanted Liston as the champion.

The President went so far as to implore Patterson not to fight Liston, but Floyd was a fair man and insisted, correctly, that Sonny had earned his chance. He would come to regret that generosity.

Making his way to the ring to face Liston, Patterson looked, as memorably put by one scribe, “like a man being led to his execution”. He couldn’t even look at Liston as the referee gave the two men their pre-fight instructions. Patterson, a fine champion, didn’t last a round.

History has been much kinder to Liston the man than his contemporaries ever were. Upon claiming the most prestigious title in all of sports, he received no recognition, no respect, no welcome home parade. The snub hurt him bitterly, and he remarked “I didn’t expect the President to invite me into the White House and play with those nice Kennedy kids, but I sure didn’t expect to be treated like no sewer rat”.

Floyd Patterson, willed on by those who wished to be rid of the champ nobody wanted, was put up to try and beat Liston in an immediate rematch. It ended in another first-round knockout.

So this was the man Cassius Clay was stepping into the ring against in February 1964.

After returning from the 1960 Rome Olympics with light-heavyweight gold, the 18-year-old Clay was possessed of an easy charm, a winning smile and plenty to say for himself. He was not what you’d call short on self-confidence.

But by the time he faced Liston, the act was starting to wear a little thin. Clay was expected, in the contemptible racial language of the time, to “know his place”. But he was his own man right from the very start. He didn’t conform, he didn’t play by the rules and he took orders from no-one.

With razor sharp reflexes and hands and feet almost as fast as his mouth, Clay was considered a promising talent. But good enough to beat Liston? He’d already been floored twice, once by a famous Henry Cooper left hook, much to the delight of the British fans.

In fact it was only some mischief from his legendary cornerman, Angelo Dundee, that bought Clay precious time to recover between rounds rom ‘Our Enry’s’ sledgehammer left.

Eight months after that narrow escape in London, Liston v Clay was on. Clay had done so much talking in the build-up that he actually managed to make the reviled Liston a more popular winner in many fans’ eyes. His vocal support for Malcolm X and the militant Nation of Islam hadn’t gone down too well either.

Come the weigh-in, in those days held on the morning of the fight, Clay went into overdrive. His hyperactive performance convinced many he was scared witless and might not even show up to fight. Liston, as usual, sat through Clay’s clowning in silence, exuding menace.

But once the first bell sounded, Clay went about stripping away that menacing aura, layer by layer. Dancing, slashing, jabbing and moving, Clay used all of his advantages in speed and height to lead the old warrior a merry dance. What followed was an utterly unexpected one-sided beating.

In the previous three years, Liston had been so dominant, so ferocious that no-one wanted to face him. The three fights he did have, including the two against Patterson, all ended within one round.

Not viewing Clay as a serious threat, he cut corners in training. Thus, as early as the fourth round, Liston was exhausted, frustrated and demoralised, barely able to lay a glove on the quicksilver Clay.

But in the challenger’s corner before the start of the fifth, there was panic. His eyes were burning and he could hardly see. The suspicion at the time, and for a long time after, was that Liston’s corner had tried some dirty trick to temporarily blind Clay by spreading liniment on Sonny’s gloves.

Yet Clay’s trainer Dundee, who knew every trick in the book, dismissed that suggestion some years later. Whatever it was, Clay got on his bike in the fifth round and managed to avoid serious punishment as an increasingly desperate Liston launched one final assault. The danger having passed, Clay re-asserted his dominance in the sixth. Liston had had enough.

As the bell rang for the start of the seventh, the champ remained seated. Clay, arms aloft, shuffled to mid-ring as a disbelieving crowd looked on. The referee raised Clay’s hand – cue pandemonium.

Clay cavorted around the ring, barely able to contain himself. This was the occasion of his famous “I shook up the world! I shook up the world! I must be the greatest!” outburst.

The great Joe Louis, a friend of Liston’s and working for TV that night, called it the biggest upset in the history of heavyweight boxing. If you ever wanted an exact definition of talking the talk, and walking the walk, Clay’s performance that night was it.

The infamous re-match, in May 1965, ended in even greater controversy. Liston was felled in the first round by the so-called ‘phantom punch’ – a chopping right hand so fast that most people didn’t see it. This was the punch that gave us that iconic photograph of Ali stood over his fallen foe, berating him to get up. Ali wouldn’t retreat to a neutral corner and so the count started late. Liston rose to his feet after around 20 seconds.

Referee Jersey Joe Walcott let the fighters continue, but was then ordered to stop the bout by officials insisting that Liston had failed to beat the count.

Debate as to whether or not Liston took a dive continues to this day. Rumours persisted of threats made to Liston by the mafia and the Nation of Islam. Those who think Liston suffered a genuine knockdown are in the minority, but he was certainly hit by a hard shot.

For Ali, his incredible journey was entering its next stage. A deeply unpopular, divisive figure, in 1967 he was stripped of his world title and banned from boxing for taking a principled stand in refusing to fight in the American war in Vietnam.

By the time he was cleared to fight again over three years later, Ali was idolised as a man who stood up to the establishment and fought for what was right, no matter the personal cost. In later titanic battles against Joe Frazier, George Foreman and Ken Norton, he displayed almost suicidal courage, further cementing the Ali legend.

For Sonny Liston there was, perhaps inevitably, no happy ending. He was found dead at his Las Vegas home in 1970, amid whispers of foul play and a mob hit.

A champion on the margins, Liston has been viewed more sympathetically since his mysterious, murky demise. Several musicians including Tom Petty, Nick Cave, The Roots, The Animals and Wu-Tang Clan have all referenced this enigmatic man, while Mark Knopfler lamented “the king they cast aside”, in his 2004 “Song for Sonny Liston” .

The mythology built up around the sport of boxing sometimes makes it hard to locate the truth. This is true of Muhammad Ali perhaps more than any other fighter, but there is no less mystique surrounding the complex and ultimately tragic figure of Charles “Sonny” Liston.

#1: Mike Tyson v James ‘Buster’ Douglas | February 11th, 1990 | Tokyo, Japan

10am on a quiet Sunday morning in Tokyo was a strange time and place for the scene of the biggest upset in boxing history, indeed arguably the biggest shock in all sporting history, bar none.

As is so often the case when big fights take place outside America, the action was scheduled at an incongruous hour to accommodate a primetime US TV audience.

In February 1990, the 23-year-old Mike Tyson was at his peak. In 1986, aged just 20, he’d become the youngest heavyweight champion of all-time, ripping the WBC title away from Jamaican hard man Trevor Berbick in two one-sided rounds.

He seized the WBA title in his next fight against James ‘Bonecrusher’ Smith, before claiming the IBF belt from Tony Tucker to become undisputed heavyweight champion just a month after turning 21.

Tyson’s path from Brooklyn street thug to heavyweight champion of the world is well documented. Both his parents were drug addicts and dead by the time he was 16. A lost child running wild in the ghetto, he discovered boxing while serving time in a youth detention centre in upstate New York.

There, he came to the attention of the wizened old boxing guru Cus D’Amato, the former trainer of the previous youngest heavyweight champion, Floyd Patterson. D’Amato was in Patterson’s corner as he lost his heavyweight crown in traumatic fashion to the unstoppable Sonny Liston.

D’Amato and his wife Camille became the orphaned Mike Tyson’s legal guardians in 1982. Ironically for D’Amato, his new charge would go on to become the most intimidating heavyweight champ since Liston, the scourge of his previous protégé Patterson.

In the mid to late 80s, Tyson laid waste to an entire generation of heavyweights, a human wrecking ball leaving a trail of destruction in his wake. No flashy dressing gown, no tassels, no gimmicks. Just his trademark black shorts, black ankle boots and cut-out towel. ‘Iron’ Mike Tyson. Even his name sounded vicious.

Thirty years ago, boxing was a mainstream sport and in the pre-internet age, Tyson was a genuine global star as famous as Madonna, Michael Jackson or Michael Jordan. This was before jail, before the bite, before all the lurid headlines.

A 1987 promotional UK tour featured an appearance on prime-time TV chat show Wogan. It revealed a rather sweet, shy, effeminate and intelligent young man quite at odds with the violent force of nature who stepped through the ropes.

Tyson continued his relentless march through the division. An aging Larry Holmes briefly showed flashes of the old magic before being ruthlessly dispatched in four. Most memorably of all, the exceptional Michael Spinks – one of the all-time great light-heavyweights – was blasted out in 89 seconds. That fight came to define Tyson at his most destructive, terrifying best.

Two more routine wins, including a fifth-round stoppage of Frank Bruno in 1989, meant that Tyson arrived in Tokyo boasting a perfect 37-0 record, with 33 knockouts.

The James ‘Buster’ Douglas story was altogether less dramatic and rather more wholesome than the chaos which enveloped the young Mike Tyson. Fortunate enough to enjoy the peace and quiet of a stable family upbringing in Columbus, Ohio, Buster’s childhood was nevertheless not without a few bumps along the way.

As a bullied, 10-year-old boy returning home in tears one day, his mother demanded he go back outside to confront his tormentor. Resolving never to be pushed around again, he started boxing under the guidance of his father, former 70s middleweight contender, Billy ‘Dynamite’ Douglas. The old man was a hard taskmaster.

Douglas forged a solid if unspectacular pro career. In a 1987 challenge for the IBF title against Tony Tucker, he was stopped in the tenth when leading on the scorecards. His most notable wins were decisions over Trevor Berbick and Oliver McCall, in the two fights immediately preceding Tyson. Buster headed for the Tokyo showdown with a 29-4 pro record.

But tragedy was to strike the Douglas camp just three weeks before the fight. Aged just 47, his mother, to whom he was extremely close, died suddenly. His handlers urged Buster to pull out of the fight, but he was determined to see it through.

Douglas has since said that that grief helped to galvanise him, and from that moment on he felt no fear. That was crucial when facing a man like Tyson, for whom intimidation was one of his principal weapons.

Another small yet significant factor was the fact that Douglas had also fought on six Tyson undercards. He’d seen him up close. He wasn’t scared by the ‘Iron ‘Mike’ image or distracted by the circus which surrounded the champion. He knew what to expect.

For all his dominance inside the ropes, outside the ring, Tyson’s life was unravelling. He’d been through a messy, expensive and very public divorce from Robin Givens. He’d been hospitalised in a car-crash and broke his hand in a bar brawl with former opponent Mitch Green.

Most damaging of all – in pure boxing terms – his long-time trainer and Cus D’Amato disciple Kevin Rooney had been ditched as Tyson came under the ever more malign influence of Don King. Shortly before the Douglas fight, Tyson had been dropped in sparring, with TV cameras there to witness it.

But despite his problems, Tyson was still seen as invincible, and potentially on his way to becoming the greatest heavyweight of all time. Douglas had been knocked out three times already, and was regarded as nothing more than a warm up before a Tyson super fight versus Evander Holyfield – ringside in Tokyo – already signed and sealed for later in the year.

Famously, Douglas was made a 42/1 underdog, in a two-horse race, by the only casino that put up betting odds for the fight. And most of the money still came in for Tyson.

“Just another day at the office for Mike Tyson, he looks almost bored, as they’re called to the centre of the ring by the referee”. So said the great Bob Sheridan, calling the fight for HBO.

But it wasn’t long before Buster had Tyson’s attention. Standing 6’4 to Tyson’s 5’10, he started strongly, throwing jabs and right crosses, showing aggressive intent and taking the fight to Tyson right from the opening bell. That by itself was something of a shock.

It became apparent from early on that this was not going to be the quick blowout that everyone had predicted. Douglas was letting his hands go, and every time Tyson did get through, Buster was quick to return fire.

With swelling around Tyson’s left eye apparent from the fourth, Douglas gained further confidence. He picked up the pace, controlling the middle rounds against a flat-footed Tyson who displayed none of his customary head movement out of his trademark peek-a-boo stance.

Tyson’s boxing skills are often underrated, but he was an excellent technician. Short for a heavyweight, he had to be. Usually giving away plenty in reach, his footwork, hand speed and head movement all had to be on point for him to get close enough to do his damage.

But by the sixth round against Douglas, he wasn’t doing much more than just plodding forward looking for the one single shot. Just about claiming the seventh, Sheridan stated that was the first round he’d given Tyson all night.

In the eighth, both boxers dished out and took some telling blows. But after being forced back on to the ropes, Tyson connected with a signature uppercut to finally floor the gutsy challenger. A shot that would have ended the fight against many others, Buster made it to his feet at the count of 9, when the bell sounded to end the round.

It looked like the writing was on the wall for the challenger, but instead that knockdown turned out to be Tyson’s last stand. A huge ninth round for Douglas swung the fight decisively in his favour, Tyson surviving several crunching combinations and barely making it out of the round, unsteady on his legs returning to his corner. Nobody could quite believe what they were seeing.

But if the sight of Tyson in trouble was shocking enough, what happened in the tenth was nothing short of seismic. 35 seconds in, Douglas unleashed a huge right uppercut stopping the advancing Tyson dead in his tracks.

The finish was emphatic, Douglas landing four more bombs right on the money to send Iron Mike Tyson crashing to the canvas. He was up just as the count reached 10, but in no condition to continue. The referee waved it off. We had a new heavyweight champion.

Those pictures of a groggy Tyson on all fours, fumbling for his gumshield, trying in vain to beat the count, somehow seem as unreal today as they did for that gobsmacked global audience back in 1990.

The sheer shock factor of the result often clouds the fact that it was an absolutely tremendous fight. Tyson, the great champion, took a ferocious beating but showed incredible heart and bravery to keep coming, defiantly searching for a way through.

He almost managed it with that knockdown in the eighth, but on this night, nothing and no-one was denying Buster Douglas. He put in an epic, punch perfect performance, and it changed his life forever.

In the fight’s aftermath there were some predictable shenanigans from Don King, who tried to claim that the fight should have been stopped after the first knockdown, as the referee gave Douglas too long to recover.

That shameful attempt to deny the worthy Douglas his deserved recognition dragged on through the courts for a while, but was eventually dismissed. The citizens of Columbus came out to salute their new, undisputed heavyweight champion.

But Douglas was not much one for the fame game, stating some years later: “There was a lot of demands. I got to do the talk shows, that was alright. But I’d have much rather been just at home, just chilling”. Buster seemed far too easy going to be a fighter.

Eight months later, he ended up facing the man Tyson was supposed to fight, Evander Holyfield. But the edge had gone. Fighting for the memory of his mother and for the opportunities his boxer father never got, Buster had put absolutely everything into dethroning Iron Mike, and had nothing left to give.

He was bombed out in three rounds by the Real Deal and promptly retired. And having pocketed $24 million for his night’s work, why wouldn’t he.

The turmoil in Mike Tyson’s private life was soon to catch up with him. Within two years of losing to Douglas, Tyson was in jail, released in 1995 to resume the second phase of his turbulent career.

As for Buster, one of boxing’s true gentlemen, after some serious health issues and a brief return to the ring, things worked out just fine. Content to blend into the background in his beloved Columbus, that’s where he remains today, as happy as can be.