Most Legendary Boxing Matches of All-Time

Mike Tyson Buster Douglas - Sports Illustrated Photo
Photo by Sports Illustrated

The Most Legendary Boxing Matches of All-Time

There is something about boxing’s mythos that makes it unlike any other sport in the world.

The well-lit ring surrounded by a darkened arena; the grandiose entrances of the fighters; and nicknames given to individual fights (like the “Rumble In The Jungle” or “The Fight of the Millennium”) conjure up vivid images of hooks, jabs, and knockdowns years after they have come to pass.

Some of these matches have become almost lore in the sports world, and we envy those that got to see any of these most legendary boxing matches of all-time as they happened.

September 14, 1923: Jack Dempsey vs. Luis Angel Firpo

Fighting long before the days of pay per view, Jack Dempsey was one of the most popular fighters in boxing history and the man responsible for the sport’s first ever million-dollar gate. The second million-dollar gate in the sport also involved Dempsey, fighting in front of 80,000 fans at the Polo Grounds against challenger Luis Angel Firpo.

After getting knocked down to one knee, Dempsey proceeded to knock down “El Toro de las Pampas” seven times. But the Argentine challenger fought back, and before the first round ended, managed to knock Dempsey out of the ring completely.

Many would argue that Dempsey’s slow return to the ring should have constituted a KO, but Dempsey fought on and in the second round knocked out Firpo in 57 seconds.

March 8, 1971: Joe Frazier vs. Muhammad Ali I

After being stripped of his heavyweight belt for refusing to join the military, Muhammad Ali returned from a 3.5-year hiatus with a vengeance, hoping to reclaim his title in his first meeting of three with world champion Joe Frazier.

The fight ebbed and flowed with both fighters suffering knockdowns, and would eventually go the full 15 rounds.

When the final bell rang, Frazier led on every scorecard over Ali, whose jaw was horribly swollen. The loss was the first of Ali’s professional career, and would set the stage for two equally unforgettable rematches.

October 1, 1975: Muhammad Ali vs. Joe Frazier III

One of the most-hyped matches in boxing history (and arguably the greatest of all-time), the Thrilla in Manilla more than gave the world want it wanted.

A rubber match between the two legends, Ali and Frazier were now so intimate with each other’s’ styles that the result this time was a 14-round battle to the death.

Photo by AP/Mitsunori Chigata

That’s only partly-hyperbolic, because after the fight was called off before the 15th round due to Frazier’s battered condition, Ali would confess that it was the closest he’d ever been to dying.

Fought in the Philippines in an arena with an aluminium roof, the ring temperature rose to a sweltering 120 °F (49 °C) under the lights and Frazier estimated that he lost five pounds during the bout.

After seeing Frazier get pummelled in the 14th and before signalling to stop the fight, referee Eddie Futch told Joe that, “It’s all over. No one will ever forget what you did here today.” And no one has.

April 15, 1985: Marvin Hagler vs. Tommy Hearns

One of the main ingredients in a legendary boxing match is consistent back-and-forth action, and that’s exactly what Hagler vs. Hearns delivered at Caesar’s Palace.

Billed as ‘The War’, the match began with the usually more methodological Hagler going straight at Hearns with a series of power shots.

Hearns replied with some big punches of his own, cutting Hagler before the round even ended.

Hagler vs. Hearns AP Images 3
Photo by AP

Hagler continued his aggressive pace into the second and third rounds, and in the latter Hearns (who later revealed that he broke his right hand during the opening round) was eventually put down after Hagler chased him across the ring landing a series of blows.

Despite not lasting three full rounds, The Ring magazine later called the fight “the most electrifying eight minutes ever.”

February 11, 1990: Mike Tyson vs. Buster Douglas

How times have changed – Tyson vs. Douglas was predicted to be such a lopsided affair that many casinos didn’t even issue odds for the match. That is something that rarely never happens now with mobile sportsbooks and popular casino games such as roulette being available to anyone with a mobile phone.

The sportsbooks that did issue odds for the Tyson vs Douglas match had Douglas as a massive 42-1 underdog.

That probably wasn’t a surprise considering that Tyson was undefeated, had never been knocked down, and had only once been in a fight longer than six rounds. Fought in the Tokyo Dome, HBO viewers tuned in to see a puzzled Tyson that didn’t know exactly how to deal with Douglas.

After getting knocked down in the 8th, the challenger would withstand a 9th round onslaught and sneak in a combination that would knockdown the Baddest Man on the Planet, who failed to get to his feet in time. 

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