ASK any boxing diehard about their favourite hypothetical fight and be prepared to do nothing but listen as they rattle on for several hours. Like football fans debating who’s greater – Pele or Maradona (or Messi or Ronaldo) – pugilism’s ardent votaries like to go deep on a topic, coming at it from different angles and perspectives like berserking switch-hitters. Certain imaginary showdowns have been theorised and bickered over for generations.

If you were a promoter in possession of a reliable a time machine – a fanciful notion, granted – what bouts would you put together? You can draw from boxing’s deep well of talent through the ages and select fighters at the height of their powers to present the most stacked card in sporting history. Five fights. One night. The Ultimate Card.

For what it’s worth, this is the one I’d make.

1. Jack Dempsey vs Rocky Marciano (Heavyweight)

Of all hypothetical collisions, not one embodies the expression ‘an unstoppable force versus an immovable object’ better than Dempsey v Marciano. My fantasy card opens with a guaranteed brawl between two of the most thunderous hitters ever to walk the face of the earth. Neither was shy about rabbit punching, hitting low and using thumbs and elbows to smash their victim to pieces, and between them the heavyweight kingpins amassed 87 KOs from 103 wins.

Dempsey and Marciano, to my mind, are almost absurdly well-matched – comparable in size, attitude and endurance. Both carried transcendent power in their gloves and armour plating seemed to overlay their sinewy bodies, such was the toughness they displayed. It’s difficult to imagine anything other than a savage, primordial battle until one man wilts under the other’s unbridled fury.

While Dempsey had a more conventional, upright style, Marciano fought out of a crouch, relying mostly on hooks and deriving bone-crushing power from his bulging calves. Almost everyone backed down when Rocky came at them but Jack was made of stone: he had a bull neck, freakish strength and, in the words of old-time fight writer John Durant, resembled a ‘two-fisted cyclone in action, all flame and power.’

A rough and relentlessly brutal opening to the Ultimate Card, wouldn’t you say?

2) Aaron Pryor vs Manny Pacquiao (Light-welterweight)

I was tempted to say Henry Armstrong vs Manny Pacquiao: Hammerin’ Hank is one of the legends of the sport, a hard-punching fireplug who once held the featherweight, lightweight and welterweight titles simultaneously. But truthfully there’s not enough footage out there of the great man doing his thing, and so I can’t envisage how a fight between he and Pacquiao might pan out (although I suspect it’d be nonstop action). In steps Aaron Pryor.

‘The Hawk’ was a stone-cold demon in his day – fearless and ferocious and quick and strong and reckless; all qualities he shared with Manny Pacquiao. You envy the matchup that has to follow Dempsey v Marciano, but if anything’s gonna keep bums on seats, it’s Pryor-Pacquiao.

What happens if the Pacquiao who iced Hatton meets the Pryor who outlasted Arguello? How would Pacquiao cope with Pryor’s unpredictability and vice versa? The Hawk generally rushed his opponents, windmilling both arms, switching attacks downstairs and up; by hounding them so continuously, he induced a kind of panic in his rivals, none of whom could hope to match his hyperactive work-rate. Pacquiao is similar, although he tends to jump in and out where Pryor rarely took a backward step. The great Antonio Cervantes famously dropped him with a right early doors, but Pryor bounced straight up and resumed beating on his man.

I’d be surprised if there were less than three knockdowns in this firefight, with both dynamos hitting the canvas.

3) Julio Cesar Chavez vs Roberto Duran (Lightweight)

For all their combined knockouts, Chavez and Duran relied on deceptively cool calculations to win bouts. Each was that rare specimen: a complete fighter – as comfortable defending against attack as launching their own.

It would be a pleasure to watch these masters engage in a high-stakes game of boxing chess. I’m not sure either met a more intelligent opponent than the other in their lengthy careers, in spite of their facing some of the brightest and best in history: DeJesus, Benitez, Hagler, Leonard, Hearns; Ramirez, Rosario, Laporte, Whitaker, De La Hoya.

A proper breakdown of this showdown probably requires a dissertation or even book-length word count, but suffice to say it would pit two of the fiercest thinkers in ring history against one another. It would be a sublime testament to the calculus at the heart of boxing and, potentially, an intriguing test of wills. Who would be the boss at in-fighting, given their fondness for slipping and sliding, blocking, parrying and countering? Duran could pick opponents’ defences like a lock, but so too could El Gran Campeón, grinding away with crippling body shots while keeping his chin smartly tucked. Who cracks harder at 135 and who dictates the terms under which the battle is contested?

Chavez was a famously slow starter, so Duran likely sweeps the early rounds. As of the fourth though, the pace surely intensifies up as Chavez’s bullying style starts to pay off. Both had iron chins so it’s unlikely either gets stopped or dropped; the real question is who stays cool in the pressure cooker? A real treat for purists.

4) Sugar Ray Robinson vs Sugar Ray Leonard (Welterweight)

Sugar Ray Leonard took his hero’s moniker, but what happens if the apprentice meets the master? Three decades separated this dyad of power-punching slicksters but has the sport ever truly graduated from the level of Sugar Ray Robinson, widely regarded as history’s greatest pugilist? Even Ali deferred to the original Sugarman. He was a handful in every respect, as natural a fighter as there’s ever been.

It’s not easy finding weak links in either man’s arsenal. Both Rays had perfect balance, blinding speed, keen natural instincts, deep reserves of tactical acumen and blockbuster power. Neither really wilted in the heat of battle (despite being outslugged by Duran, Ray fought spiritedly till the end; and the unbearable heat did for Robinson more than Maxim) and each could be as mean and merciless as they were evasive and balletic.

To my mind, Robinson had a laser-eyed focus while Leonard occasionally became a victim of his own success, admiring the effect his punches were having on opponents. By comparison, Robinson stalked the ring like a panther, ready to fire off three, four or five rounds at any moment: punches that could flatten you in the blink of an eye.

While this spectacle would doubtless be wonderful to watch, it’s the only one on my card in which I see a clear outcome: Ray Robinson by decision. He probably never met a mover as gifted as Leonard, but I see SRL struggling with Robinson’s combination of speed and power just as he struggled with Hearns’. I also see the judges favouring Robinson’s uptempo, front-foot style of boxing over Leonard’s, which could be more sporadic. Either way, this would be a compelling battle of boxing’s most brilliant fighting machines.


5) Muhammad Ali vs Mike Tyson (Heavyweight)

Ali v Tyson is the most debated hypothetical fight in the boxing canon. Three-time heavyweight champion Ali – the division’s figurehead in its golden age – versus the youngest titlist in history, the brutalising force of nature who cut a merciless swathe through the sport in the late ‘80s. It’s perhaps the ultimate clash of styles and like all good main events, it’s the one which spectators would anticipate most keenly.

We know which version of Tyson steps through the ropes here: the Hercules who sat atop the heavyweight pile, unbeaten and seemingly unbeatable at the peak of his powers. But which Ali? Late 60s Ali and mid 70s Ali are very different creatures, the former relying largely on graceful footwork, the latter on tying opponents up, counterpunching with his back to the ropes and sheer defiance over the course of 15 rounds.

Few argue that late 60s is peak Ali, but there’s also a case to be made that Muhammad became more complete after his lay-off, in that he learned how to compensate for his slowing legs, grapple with bigger, stronger men and steal breathers in gruelling fights. In any case, I’m going with young Ali to face Tyson: the one who cut Liston to ribbons, who mullered Zora Folley, Floyd Patterson and, memorably, the ‘Big Cat’ Cleveland Williams.

Tyson himself is on record as saying he doesn’t beat Ali, prime for prime, but that’s an old, reflective, retired Mike speaking. His younger self is surely a different proposition. Be that as it may, this one pits the wrecking ball Kid Dynamite against a sharp-punching Louisville Lip. It’s more than that, though: more than puncher v boxer, aggression v movement, strength v skill. Tyson-Ali can’t be put in such a limited category. Because in addition to blowing through buildings, young Tyson was expert at slipping jabs, closing distance, working the body and bringing a jackhammer uppercut through his opponent’s guard. By the same token, Ali was more than a gifted mover – he could lay guys out, mark them up, make them quit.

Does the young Ali deter the rushing bull with his long punches, or does Tyson wear him down with a hounding attack? Does Iron Mike’s rapid head movement trump The Greatest’s blinding hand speed? Perhaps Ali slows after four or five rounds and Tyson gets to him late. Maybe it’s the other way around. The thing about hypothetical fights is, no-one knows.

One thing’s for sure, Ali-Tyson would be as engrossing as any match ever witnessed. I got Ali by UD.

The time machine’s all yours: what five blockbusters make up your dream card? Comment below or kickstart the debate on social media.