Top 10 best duologies in boxing history

Alisa Barladyan
21 Mar 2022

The history of professional boxing is full of cases where the paths of certain fighters have repeatedly crossed. As a rule, this happened when the first fight didn’t dot the T’s or had a dramatic ending. This time wants to recall the most remarkable duologies in the history of boxing. It’s impossible to fit all the great confrontations in one article. However, we tried to select those dilogies that at one time made a huge impression on fans and stood out for their historical value.

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Holyfield - Tyson
Holyfield - Tyson

Evander Holyfield - Alex Stewart

The top opens with an incredibly spectacular battle between Evander Holyfield and Alex Stewart. Their first meeting took place in November 1989. Evander only moved up to heavyweight after conquering the cruiserweight. Holyfield was steadily moving towards superstar status. He had a perfect track record, however, as Alex Stewart had as well. The duel can be described as a "battle in a telephone booth". The battle was on a collision course at close and medium distances. It was a real "old school" fight performed by Evander and Alex. This fight may not be familiar to modern boxing fans, but we highly recommend watching it. By the way, Holyfield celebrated the TKO victory in the eighth round only after the doctor didn’t allow Alex to continue fighting.

The rematch between Holyfield and Stewart took place in June 1993. Like the first time, the fight was an example of real courage and boxing professionalism. Combination work, defensive actions, stamina - all were at the highest level. Of course, Holyfield became a more high-class fighter, which allowed him to win the final victory. However, the resistance that Alex Stewart put up is what makes this dilogy so interesting.

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Evander Holyfield - Mike Tyson

The next position in the top is occupied by a real boxing classic and again with the participation of Holyfield. This time we remember his legendary confrontation with Mike Tyson. All advanced boxing fans are aware of how it ended. But for those who don't know, let us tell you briefly. In 1996, Evander entered the fight against Tyson in the status of a huge underdog and created an upset, knocking out Mike in the 11th round. Every self-respecting fan should watch this fight, because that's how the great champions fought. By the way, at that time it was the highest-grossing fight in boxing history, with 1.59 million PPV sales.

Evander's first fight with Mike shocked the boxing world so much that the fans wanted a rematch, and the org-men were happy to arrange it. The financial performance of the second meeting broke the previous record. PPV sales amounted to 1.99 million. But the fight ended in a huge scandal, which, however, only added to the frenzied popularity of both. We recall that Evander regularly hit Tyson with his head, for which "Iron" Mike bit off a piece of his ear. Then a fight ensued, in which Mike single-handedly almost destroyed the entire MGM Grand security squad and the Las Vegas Police Department. Whatever it was, but this dilogy has become legendary.

Chris Eubank - Nigel Benn

It has to be mentioned about the two fights of iconic British boxers Chris Eubank and Nigel Benn. Their first fight took place in November 1990. The fighters had a personal dislike for each other, which they carried into the ring. Both didn’t want to give in to each other under any circumstances. This fight is the pride of British boxing and a real feast for the fans. The evasive and fast Eubank made a real game for the "Dark Destroyer". The fight ended in the ninth round with Chris's victory, but it turned out to be so exciting that their rematch was only a matter of time.

Three years later, the paths of the athletes crossed again. This time they fought not at middleweight, but at super middleweight. By the time they met again, both had achieved world-class superstar status. The rematch ended in a well-deserved draw. Why should you watch this duology? Both Britons showed their unique style, which you definitely will not find against the background of the modern majority of the same type of boxers.

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Carl Thompson – Chris Eubank

Another duology and again with the participation of Briton Chris Eubank. It happened that in his career there were many spectacular battles, many of which were remembered by the fans. All it’s all because Chris fought is the best. At the end of his career, namely in 1998, "Simply the Best" ventured into the ring against light heavyweight champion Carl Thompson. In the 12-round "swing" the reigning champion Thompson celebrated the minimum victory.

The fighters found only one "hellish meeting" insufficient. Just three months later, the crazy Brits staged an act of revenge. The second fight turned out to be the most competitive again, but age took its toll. Eubank conceded ahead of schedule in the ninth round, after which he hung up his gloves.

Bernard Hopkins – Jean Pascal

A relatively modern duology began at the end of 2010. Then the world light heavyweight champion Canadian Jean Pascal defended the titles from the encroachments of the legendary Bernard Hopkins. At the time of the fight, the "Executioner" was 45 years old. Pascal is only 28. Critics, who constantly reproached Hopkins for his unspectacular style, rested that evening. Bernard was twice knocked down but managed to equalize the fight. Although the "Executioner" didn’t reach the victory. The final draw only warmed up interest in their revenge.

n mid-2011, the second fight took place, in which experts predicted defeat for the 46-year-old Hopkins. Still, the difference of 17 years didn’t allow looking in favor of Bernard. However, the veteran showed a real master class. Hopkins boxed, as they say, without a hitch. The victory in the rematch allowed him to become the oldest champion in the history of professional boxing. He will surpass his record later, but that's another story.

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Diego Corrales – Jose Luis Castillo

How not to mention the crazy fight of Jose Luis Castillo and Diego Corrales? Their first meeting took place in May 2005, and many experts consider that fight the most dramatic fight in history, and the 10th round the greatest round in boxing. Corales was knocked down twice, got up twice and eventually finished José Luis.

Unfortunately, the second fight turned out to be less competitive. Six months after the incredible first meeting, it was the Mexican who got the best shape. Jose Luis Castillo knocked out the opponent in the fourth round, taking revenge from Diego Corrales.

Shane Mosley - Oscar De La Hoya

Another duology from the "golden era of the 2000s". At that time, the names of such fighters as Oscar De La Hoya and Shane Mosley were on everyone's lips. In June 2000, Shane decided on a desperate step; he jumped two weight classes up to fight Oscar. Although experts predicted defeat for Sugar Shane, he proved the opposite. The 12-round high-tech war ended with Moseley's victory. Lightweight and welterweight divisions were booming at the time, thanks in part to athletes like Oscar and Shane.

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In September 2003, a rematch took place, in which Shane again celebrated the victory by decision. "Sugar" won this diology against Oscar with a score of 2-0, but this doesn’t negate the fact that their fights were as close and exciting as possible.

Ronald Winky Wright – Shane Mosley

Old-school fans are well aware of the Ronald Winky Wright vs. Sugar Shane Mosley rivalry. Their fights took place in 2004. Then everyone bet on Shane, because Ronald wasn’t yet so famous, but they were wrong. Winky Wright's unexpected triumph propelled him into the elite boxing pro.

The collection of every lover of beautiful, technical fights also contains the second meeting between Shane and Wright. This fight was more competitive, although it also ended in a decision victory for Ronald. For professional boxing, the value of this dilogy is that skill and boxing intelligence come first here.

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Oleg Maskaev - Hasim Rahman

The incredibly dramatic battle between Russian Oleg Maskaev and American Hasim Rahman is also gathering dust somewhere on the shelves in the collection of the best fights in history. The first fight took place in November 1999 in the United States. Maskaev was in the role of an underdog and lost a little during the meeting. But in the eighth round, Oleg struck a blow, after which Rahman flew out of the ring and almost crushed the entire refereeing team in the ringside. After that, a grandiose fight began, which couldn’t be calmed down for a long time. It’s interesting that there was a funny dialogue between the boxers at the pre-match press conference. Hasim said, "I will never lose to a white man." To which Oleg replied: "I'm not just white, I'm Russian."

No matter how cool the confrontation between these fighters was, the revenge managed to surpass the first battle.

In August 2006, their paths crossed again. This time, Hasim Rahman was already in the status of world champion. Oleg was again content with the status of an underdog.

The course of the fight really showed Rahman was a more skilled and prepared fighter. Hasim controlled the entire fight almost to the very end. Maskaev, on the other hand, rested solely on strong-willed qualities. Before the final 12th round, the champion either ran out of steam, or believed in victory too early. While in the corner of the Russian boxer there was an incredible psychological pump. The second repeated to Oleg: "For dad, for mom, for daughters, for the Motherland."

It was in the last round; Oleg turned the course of the battle in his favor. First, he knocked down Hasim twice, after which he scored a tired Rahman at the ropes. It was a shock! By this day, that victory is the most dramatic in the heavyweight division over the past 20 years.

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Joe Louis – Max Schmeling

The confrontation between Louis and Schmeling positions itself as the first megafight in the history of boxing. Then the battle of the two fighters grew into much more, namely politics. The confrontation of two countries with different types of government, worldview and social foundations. All this was against the backdrop of the greatest battle of the time, Max Schmeling and Joe Louis. And, to the surprise of many, Max won the first fight (1936), stopping the American in the 12th round. However, two years later, Joe Louis came out in very good physical shape, unlike the previous meeting. In the first round, he literally beat the German athlete. It was the best performance of the great Brown Bomber's career.

Sugar Ray Leonard – Thomas Hearns

There is no doubt that the greatest duology in the history of boxing is the fight between Ray Leonard and Tommy Hearns. It is not every day that we have the opportunity to see the best representatives of the pound for pound rating fight. Of course, such fights are not always spectacular. But the battle between Tommy Hearns and Ray Leonard in 1981 was just that. Sugar Ray won by TKO in the 14th round. But what was it like? There is no point in talking about this battle, it must be seen.

The revenge took place after a long eight years. Both athletes passed their peak condition, but this didn’t stop them from making a grandiose spectacle. Successful moments passed from one to another. The fight ended in a fair draw. Today we are happy to review these fights and thank the great fighters for the newly presented emotions.

It’s worth mentioning such duologies as Muhammad Ali - Sonny Liston, Muhammad Ali - Henry Cooper, Arturo Gatti - Ivan Robinson, Lennox Lewis - Hasim Rahman, Lennox Lewis - Evander Holyfield, Manny Pacquiao - Marco Antonio Barrera, Shane Mosley - Fernando Vargas and others.

It’s a pity that modern boxers are very spoiled by big fees and are in no hurry to enter the ring with worthy opponents. But let's hope that in the future athletes will return to the principle of "the best fights the best" and will please us with a huge number of great battles.

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