10 DREAM boxing fights that never happened

Boxing is one of the most famous and well-documented combat sports in human history. Furthermore, boxing reigned supreme before the rise of MMA, considered a blood sport in the past. Sadly, throughout the past 50 years, boxing has lost many dream fights.

Imagine the excitement and anticipation surrounding two boxing legends stepping into the ring together, ready to battle it out in the fight of a lifetime. These dream matchups have fueled the imaginations of fans for years. Unfortunately, these fights never came to fruition for various reasons, such as weight class, failed negotiations, or early retirements.

However, even though several fights never happened, it’s still interesting to imagine the intensity of these legends facing off. Hence, let us delve into the what-ifs and hypotheticals of the boxing world as we explore these missed opportunities.

10. Roy Jones Jr. vs. Nigel Benn

A hypothetical matchup between Roy Jones Jr. and Nigel Benn remains a fascinating clash between two skilled and powerful fighters from the 1990s. Due to the lack of luck, it never happened. Some of the new generation remembers Benn for the tragic fight against Gerald McClellan. Benn could punch the lights out of anyone. Jones Jr. had one of the best hand speed and reflexes that saw him win titles in middleweight, super middleweight, light heavyweight and heavyweight.

The hypothetical matchup between Roy Jones Jr. and Nigel Benn would likely be a high-stakes encounter. Furthermore, the fight would showcase the contrasting styles of a defensive master and an aggressive power puncher.

9. Roberto Duran vs. Alexis Arguello

A matchup between Roberto Duran and Alexis Arguello remains a dream boxing match for many. Furthermore, the fight has all the attributes of a closely contested battle between two legendary fighters from different weight classes. Both Duran and Arguello were exceptional in their own right, showcasing distinct styles and skills.

The battle highlights the best boxers of Latino origin. Both athletes had tremendous knockout powers. Either one could knock each other out. It would have featured intense back-and-forth action had they faced each other.

8. Oscar De La Hoya vs. Kostya Tszyu

A hypothetical matchup between Oscar De La Hoya and Kostya Tszyu would have featured a unique storyline. Tszyu is considered a national sports hero by many in Australia. De La Hoya won the gold medal for the US. Hence, a dream matchup would have featured two national heroes of two nations battling it out.

Given the skills and durability of both fighters, the bout could potentially end in two ways. De La Hoya could win on points due to his boxing skills. Alternatively, Tszyu’s power might lead to a late-round stoppage if he successfully breaks down De La Hoya’s defense.

7. Riddick Bowe vs. Lennox Lewis

A hypothetical matchup between Riddick Bowe and Lennox Lewis intrigues the boxing fans very much. Heavyweight champions from the 1990s, like Mike Tyson and Evander Holyfield, faced off against Lewis. However, Lewis did not face Riddick Bowe. They were known for their size, skill, and accomplishments. Though, they did fight each other as amateurs, a professional bout did not happen.

The outcome of a hypothetical matchup is highly speculative. Opinions would vary on who would win differ among boxing enthusiasts. Both fighters were exceptional in their own right. It is one of the matchups that failed to materialize that haunts passionate boxing fans.

6. Sugar Ray Leonard vs. Aaron Pryor

A hypothetical matchup between Sugar Ray Leonard and Aaron Pryor would have resulted in a fascinating encounter. The matchup pits two legendary fighters from the 1980s against each other. Leonard and Pryor were dynamic and exciting in their own right, but they operated in different weight classes.

Subsequently, Leonard was known for being a versatile welterweight, and Pryor was a dominant light welterweight. Furthermore, Leonard’s boxing IQ and versatility versus Pryor’s relentless pressure and power would create a captivating contest.

5. Tyson Fury vs. Vitali Klitschko

Both fighters are huge heavyweights. Tyson Fury is known for having exceptional height and reach. However, Vitali Klitschko‘s powerful right hand and solid jab were among his most effective weapons. Hence, if he could establish his jab and land significant right hands, it could potentially disrupt Fury’s rhythm.

However, Tyson Fury remains capable of nullifying Vitali. The best version of Fury could make it an equal fight against the elder Klitschko brother. The outcome could be a decision if the fighters engage in a tactical battle. Alternatively, a stoppage could occur if one fighter manages to land significant, fight-changing blows.

4. Vladimir Klitschko vs. Lennox Lewis

Vladimir Klitschko and Lennox Lewis reigned as dominant heavyweight champions. Both Klitschko and Lewis were intelligent fighters capable of making strategic adjustments. Though Lewis fought and defeated Klitschko’s elder brother, a fight between him and Vladimir did not happen. Vladimir entered his prime as Lewis retired from the sport.

The boxer who could adapt more effectively during the fight might gain an advantage. Klitschko fights with an unbeatable strategy, whereas Lewis has a way of disrupting the rhythm of his opponent. It is another dream fight that didn’t happen because of the age difference.

3. Canelo Alvarez vs. Manny Pacquiao

It would be a significant event if a hypothetical matchup occurred between Canelo Alvarez and Manny Pacquiao. They have major accomplishments and immense popularity. A bout between the two would have broken PPV records and minted massive revenue. Furthermore, both fighters fought against Floyd Mayweather, but they never fought each other.

The outcome could be a decision if the fighters engage in a closely contested battle. The judges would score it based on effective aggression, ring generalship, and clean punching. The toughness and mentality of Prime Canelo and Prime Pacquiao would make it impossible to end the bout in a stoppage. It is a shame that the fight did not happen between them.

2. Muhammad Ali vs. Rocky Marciano

Both fighters are considered among the greatest heavyweights of all time, but they fought in different eras with distinct styles and approaches to the sport. Muhammad Ali‘s speed and agility against Rocky Marciano‘s power and relentless pressure remain a dream matchup. Furthermore, Ali’s ability to move and avoid punches, versus Marciano’s pursuit and determination to close the distance, would shape the fight.

Rocky Marciano remains one of the few athletes to retire with an undefeated record. He used to at least a dozen miles a day. His conditioning remains otherworldly. Ali had once talked about the prospect of facing off against Marciano. Only one fight could have topped this dream fight, and that is number one on the list.

1. Muhammad Ali vs. Mike Tyson

A hypothetical bout between Muhammad Ali and Mike Tyson is one of the most debated and popular dream matchups in boxing. This fight never happened because both boxers were active in different eras. Moreover, Ali was forced into retirement due to his illness. Ali’s footwork and boxing IQ might have troubled Tyson early in the fight.

However, Tyson’s power and aggressive style could potentially lead to a knockout victory in the later rounds. It could turn into a battle of wills, with Tyson trying to land power shots and Ali attempting to outbox and outmaneuver Tyson. Also, imagine if Cus D’Amato coaches Tyson in the dream fight. Everything about the fight has a different type of aura compared to other dream fights that never happened.

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