20 Of The Best And Biggest Fights In Boxing History

Boxing remains one of the most popular sports globally, and the top boxers remain some of the highest-paid athletes around. There’s nothing like a high-level boxing match featuring two talented fighters with technically even skills. What typically ensues is a fast-paced chess match where attributes like toughness, determination, and the will to win often determine the victors.

This article will explore some of the best boxing matches that have ever taken place. Try to watch them all to up your boxing IQ and appreciation for the sport. 


The 20 Best Boxing Matches In History

Let’s dive right into our list and see which fights make the cut:


1) Evander Holyfield vs. Mike Tyson II

Evander Holyfield shocked the world when he defeated Mike Tyson in 1996 to win the WBA heavyweight title. That led to the highly anticipated rematch between the two at the MGM Grand Garden in Las Vegas. 

Mike Tyson’s fans were sure Holyfield’s first win was a fluke, but Holyfield proved otherwise during the rematch, using his jab to keep Tyson away and dominating the exchanges. Frustrated, Tyson committed an act he could never outlive, biting off part of Holyfield’s ear. 

It was one of the most insane moments in boxing history, and it got Tyson disqualified, marking his second loss to Holyfield. The bite also led to Tyson losing his boxing license. He was eventually able to get it reinstated, and he went on to have many more professional fights. 


2) Erik Morales vs. Marco Barrera

The first round of this historic matchup was one of the most action-packed rounds in boxing history, with both fighters landing their fair share of punches. Things hadn’t cooled down by the fifth round of the fight as Morales unleashed a vicious barrage on Barrera. Just when it looked like Barrera was in trouble, he fired back with ferocious punches of his own, sending the arena into a frenzy. The entertaining showdown earned both men the Ring’s Round of the Year award. 

Morales went on to win the fight by split decision, which led to two more fights between the two. The classic trilogy between Morales and Barrera remains one of the most entertaining trilogies in boxing history. 


3) Rocky Marciano vs. Joe Walcott

This historic matchup had the entire boxing world divided leading up to it. Many, including Walcott, thought Marciano was overhyped and overrated. Walcott was so confident it would be an easy matchup for him that he asked for his name to be taken out of boxing’s record books if he lost to Marciano. 

Walcott came to fight when the opening bell rang. He handed Marciano the first knockdown of his career, and Marciano was heard complaining that he couldn’t see by the seventh round. Both men were pretty busted up by that point. 

Marciano memorably turned things around with a huge right hook that left Walcott unconscious as he fell into the ropes. 


4) Floyd Mayweather Jr vs. Manny Pacquiao

The Mayweather vs. Pacquaio super fight was one of the most anticipated fights in boxing history. It took almost a decade for both men to finally come to terms despite the high fan demand for the fight. The fight put up historic numbers, pulling $410 million via pay-per-view, making it the highest-grossing boxing match ever. 

Many fans thought the fight lived up to the hype, while others felt disappointed. It was a classic fight, as Mayweather put out a lot more offense than usual. He went right after Pacquaio from the opening bell, landing hard rights that left him second-guessing himself. 

Mayweather easily took the first few rounds before Pacquiao finally found his rhythm in the fourth round. Mayweather dominated most of the fight, earning an unanimous victory against his arch-rival. 


5) Carmen Basilio vs. Tony DeMarco II

The first fight between these two went the distance, and Basilio emerged victorious, winning Demarco’s NYSAC, NBA, and Ring welterweight titles. 

Demarco vowed to reclaim his titles during the rematch, and he got off to a good start winning the opening round. Then Basilio broke his left hand during the second round. DeMarco was on his way to victory when Basilio sent him to the canvas during the final round. DeMarco willed himself back to his feet, but Basilio never gave him a chance to recover, sending him back down to the canvas moments later to end the fight. 


6) Deontay Wilder vs. Tyson Fury I

The first fight between these two turned out to be one of the most entertaining fights in boxing history. Going in, everyone knew Fury was the more technically sound boxer. He quickly established himself as the better fighter, winning most of the rounds on points, but Wilder kept things close.

Wilder kept things interesting with a knockdown in the ninth round, and it looked like he had secured the victory in the 12th round when he sent Fury to the canvas with a hard shot. Miraculously, Fury managed to get back up and finish up the fight. The bout was called a split draw. 

Fury and Wilder fought two more times, with the former winning both bouts via knockout. 


7) Sugar Ray Leonard vs. Marvin Hagler

Leonard had only a single fight in about five years heading into his showdown against Hagler. Hagler was the favorite heading into the contest, but things played out differently from what many people expected. 

Leonard took control of the fight early on, and he finished strong, earning himself a split decision victory. It was an entertaining bout that ended in one of the biggest upsets in boxing history. 


8) Israel Vazquez vs Rafael Marquez III

Vasquez and Marquez shared a ring four times, and they were all quite entertaining. The first fight between the two was a wild brawl with both fighters showcasing their huge hearts. Marquez emerged victorious after their first showdown, but Vazquez got some payback during the rematch, winning via split decision. The second fight also earned the pair the Ring Magazine Fight of the Year award. 

The third fight between these two was highly anticipated, given how close and entertaining the first two fights were. The fight lived up to the hype, earning them another Fight of the Year award. Both men brawled it out for 12 rounds, with Vasquez suffering deep cuts around his eyes. Vasquez went on to win the fight via split decision. 


9) Zolani Tete vs. Siboniso Gonya

This fight earned its spot on our list due to its historic relevance. Tete was defending his WBO World bantamweight title against Gonya, but the fight didn’t last long. Tate only needed 11 seconds to knock out Gonya with the only punch thrown during the fight. The finish still holds the record for the fastest knockout ever in a world title boxing match. 


10) Sugar Ray Leonard vs. Roberto Duran II

This was arguably the biggest super fight ever made at the time. Duran defeated Leonard via unanimous decision the first time they shared a ring, but Leonard turned things around during the rematch. He took control from the start and outclassed Duran, forcing him to verbally quit during the eighth round. With the victory, Leonard reclaimed the Ring and WBC welterweight belts. 


11) Andy Bowen vs. Jack Burke

Here’s another fight that made our list for mostly historic reasons. It still holds the record for the longest professional boxing match in recorded history, lasting 110 rounds. Burke broke both of his hands during the fight, and both men walked out of the ring about ten pounds lighter than they were when they stepped inside it. 

After over seven hours of action, the referee eventually had mercy on both fighters, declaring the fight a draw. 


12) Sugar Ray Robinson vs. Jake LaMotta VI

These two boxing legends fought each other six times, and their sixth fight ended up being the most memorable and entertaining. The fight was dubbed the “Valentine’s Day Massacre,” as Robinson viciously beat LaMotta during the later rounds. The fight was officially stopped during the 13th round due to the damage LaMotta had taken.


13) Marvin Hagler vs. Tommy Hearns

Many boxing experts view this showdown as the most entertaining middleweight fight in boxing history. Both men came out aggressively, and it didn’t take long for them to hurt each other. It was action-packed for its entirety until Hagler brought the contest to an end with a huge punch that sent Hearns to the canvas. Those three rounds were enough to earn both men Fight of the Year honors for 1985. 


14) Julio Chavez vs. Meldrick Taylor 

The two put on an impressive display the first time they shared a boxing ring. Chaves sported a 68-0 record at the time, and he was the reigning WBC light-welterweight champion. Experts expected another dominant performance from Chavez, but that’s not what happened. 

The action was exhilarating, with Taylor getting the better of the exchanges for most of the contest, shocking the crowd. However, Chavez showcased the incredible heart he was famous for, scoring an epic knockout during the final round of their title bout with only two seconds left in the contest. 

How’s that for theatrics?

Taylor was ahead on the scorecards up until that point, and he would have most likely won a unanimous decision if he had been able to survive for two more seconds. That would have made him the first man to defeat the legendary Chavez. 


15) Jack Dempsey vs. Luis Firpo

Firpo made boxing history, becoming the first Latino American fighter to fight for a world heavyweight title. Dempsey was the reigning NYSAC heavyweight champion, and he was the favorite heading into the fight. Firpo struck first early in the contest, sending Dempsey to the canvas during the opening seconds of the first round. 

That made Dempsey mad, and he went on to knockdown Firpo seven times during the same round. Firpo landed his second knockout towards the end of the round, sending Dempsey out of the ring. That would have been enough to end the fight these days, but boxing was a different sport in the early 20th century. 

Dempsey recovered from the second knockdown and put Firpo away during the second round, retaining his world title. Both fighters scored 11 knockdowns during the fight, a modern-day boxing record that remains unbroken. 


16) George Foreman vs. Muhammad Ali

Muhammad Ali became the world’s heavyweight champion for the second time when these two met in Zaire. Ali went into the fight as an underdog, with many experts picking Foreman to overwhelm him with his strength. It was one of the most hyped fights in boxing history, and it still managed to exceed all expectations. 

Ali was at his very best during the build-up to the fight, with his constant verbal onslaught on Foreman. Foreman was ready to take his head off when the opening bell rang, but that was what Ali wanted all along. Ali used an interesting tactic that he later called the “rope-a-dope” to tire Foreman out before picking him apart. It worked like a charm, and Ali regained his status as the heavyweight champion. 


17) Sugar Ray Leonard vs. Thomas Hearns

Hearns and Leonard were two of the biggest names in boxing heading into this classic fight. The match turned out to be an evenly matched affair, with both men having their moments until the sixth round when Leonard sent Hearns to the canvas. 

Leonard scored a second knockdown during the 13th round, stunning Hearns with a cross and following up with a barrage of punches. The beating continued during the 14th round, forcing the referee to stop the contest. 


18) Joe Frazier vs. Muhammad Ali 

This was one of the most anticipated fights in the 20th century, and it was even billed as “The Fight of the Century.” Both men were undefeated when they squared off against each other for the WBA, WBC, and Ring heavyweight titles. 

Ali got the better of the exchanges early in the championship bout, but Frazier wasn’t about to go down without a fight. He floored Ali with a massive right hook that ended up stealing the fight. Ali miraculously got back to his feet, but that wasn’t enough to avoid his first loss as a professional fighter. The loss also led to one of the greatest rivalries in boxing history as Ali made it his life mission to avenge it. 


19) Arturo Gatti vs. Micky Ward 

This classic matchup featured two fighters who bit down on their mouthpieces and went to war. Gatti took control early on in the slugfest, but Ward turned things around in the eighth round with some heavy shots that almost put Gatti away. Fortunately for the Gatti, the bell rang just in time to save him. 

Both men kept up the pace for the rest of the night, throwing hard shots until the final bell rang. Ward was awarded the decision afterward. 


20) Muhammad Ali vs. Joe Frazier III

The “Thrilla in Manila” was one of the most anticipated events in boxing history. It featured two legends with a lot of history between them. Frazier won the first contest between the two and ruined Ali’s undefeated record. Ali got payback during their rematch, handing Frazier his second loss as a professional. 

The world couldn’t wait to be the rubber match between the two. 

Ali got off to a solid start after, but Frazier found his range as the fight progressed, chopping Ali down with powerful blows. Ali eventually regained control, and his stiff jabs led to Frazier’s eyes being closed by the 14th round, forcing his corner to throw in the title.  


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