Here’S A Look At Some Of The Greatest Boxing Fights Makes Us Wish They Fought One More Time Before They Died

Here’s a look at some of the greatest boxing fights that we’ll only get to see in our imaginations.


In his prime, Tyson was a dominating force of nature, a menacing villain who tipped almost into caricature. Ali, on the other hand, was a natural showman, a charmer, a media presence and also a more skilled and more technical fighter than anyone Tyson ever had to face in the ring.

The contrast in their styles and personalities would make it a dream fight even without the fact that they are two of the greatest boxers who ever lived. How awesome would this be?


Vitali and Wladimir Klitschko made boxing history when they became the first brothers to simultaneously hold world heavyweight boxing titles. However, the two giants never unified those belts, for a simple reason: they had vowed to their mother that they would never fight each other. As a result, the most highly anticipated heavyweight bout of the past 20 years never happened. For the sake of the Klitschko family gatherings, that’s probably just as well, but it’s too bad for the rest of the world.


Pretty Boy Vs. Kid Dynamite: Mayweather Against Tyson, In Their Primes -  Boxing News 24

Yeah, so technically they did actually fight. But the boring debacle we were subjected to in 2015 was nothing compared the dream fight we all wanted to see back in 2009. That’s when Pacquiao was in his prime, winning his sixth title in his sixth different weight division. We’ll always dream about the fight that might have been, if only Mayweather had been willing to put his money where his mouth was.


Despite retiring in 1927, Jack Dempsey still remains one of the most popular boxers in history. His legend has only really been eclipsed by one man: Joe Louis, who held the heavyweight championship for 12 years while successfully defending his title 25 times. Dempsey once said that he was glad he never had to face Louis in the ring, but he was the only person in the world who felt that way. Even now, a Dempsey versus Louis fight would unquestionably be the bout of the century. If only that cloning technology would catch up to our dreams.



Sugar Ray Leonard announced his first retirement in 1982. Pryor dominated the super lightweight division in the early 1980s before moving up to welterweight and claiming that title as well. That put him right in Leonard’s wheelhouse, but by the time Leonard was ready to come out of retirement again, Pryor had hung up his gloves. What if?


Mike Tyson and George Foreman were two of the angriest, fiercest, heaviest hitters in the history of boxing. Foreman did actually try to land a fight with Tyson in the 1990s, when they were both well past their peak, but it never materialized. If they ever get that time machine invented, everyone knows what the first order of business is.


Arturo Gatti vs Micky Ward 4 Full Fight - Fight Night Champion Simulation -  YouTube

“Irish” Micky Ward and Arturo “Thunder” Gatti are forever linked in boxing lore thanks to one of the greatest rivalries of all time. Their first match was the 2002 fight of the year, with the ninth round called the round of the century. And their third match was again the fight of the year, for 2003. In both cases, each fighter ended up in the hospital following the bouts. Which may explain why there was never a fourth showdown; indeed, the fights were the final three of Ward’s career, as he retired after their last showdown. Sadly, Gatti died a few short years later, removing any possibility of a comeback rematch between the pair, so the dream of Ward vs. Gatti Part IV will always remain just that: a dream.


Marciano retired with his perfect 49-0 record in 1956; Ali made his professional debut in 1960. Though Marciano never seriously considered coming out of retirement to fight Ali, the two did meet in 1969 for a faux fight: they sparred on camera for a televised special called The Superfight: Marciano vs. Ali, which featured a computer simulating the results of the bout. Naturally, the computer declared it a draw, with different simulations showing both Marciano and Ali winning the bout.


Finally, I just have to wonder how cool it would be to see the fictional Rocky Balboa square off against his real life inspiration, the scrappy, perpetual underdog Chuck Wepner. Wepner famously knocked down the heavily favored Muhammad Ali in a 1975 title bout before eventually being counted out at the end of the 15th round. He also later sued Sylvester Stallone over the appropriation of his story for the Rocky films, adding some extra spice to this potential matchup. It’s not clear who would win in a fight between Balboa and Wepner, but one thing is certain: there wouldn’t be any losers.


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