Past vs Present Boxing Dream Fights

Because the world of sports has such a deep and storied history, there will always be debates about who the greatest athletes are as every era is different. As sports and the athletes themselves continue to evolve, fans and pundits alike evolve as well demanding a new level of excellence with time. With that comes conversations about what would happen if great athletes of the past faces off against present greats. Whether it be LeBron vs Jordan, Tom Brady vs Joe Montana, or Usain Bolt vs Jesse Owens, there is always a past vs present dream match. While we can’t go back in time and see those amazing dream encounters, that does not stop the heated debates that persist in about who would win between great athletes of the past versus the current stars. The sport of boxing is no different with its history going back to the late 1800s filled with amazing fighter across its many weight classes.

The saying in boxing is “styles make fights” and there is so many different styles associated with the sport of boxing. While most would consider the potential for a knockout to be the most exciting aspect of boxing, the sport has so much more to offer than just that. In fact, some of the best fights are the ones where both fighters trade punches for the full 12 rounds without touching the canvas. At the end of the day, that’s what makes the sport so fun because anything can happen when two of the best fighters in the world step in the ring to face each other. With that being said, we’re here to talk about some of the biggest dream fights the sport of boxing has to offer where we put the biggest stars of boxing today against the stars of yesteryear.

Here are the Biggest Past vs Present Boxing Dream Fights!

Gennady Golovkin (41-1-1) vs Marvin Hagler (62-3-2)

Of all the middleweight boxers in the history of the sport, no one embodies the division more than Marvin Hagler and Gennadiy Golovkin. Both men are well-known for their amazing power with Golovkin’s career knockout percentage currently sitting at 84% while Hagler’s was 77%. Gennadiy Golovkin became well-known for winning 23 consecutive fights by knockout from 2008 to 2017 with 17 of those fights coming during world title matches. He On the other hand, Marvin Hagler reigned as undisputed champion for over six years winning 12 of his 13 title fights by knockout. They are also known for being two of the pound-for-pound toughest fighters in boxing history. In their careers, neither man never has nor never been knocked out and Hagler was only dropped once in his career. This would be the ultimate middleweight dream fight filled with amazing power, endurance and captivating action.

Evander Holyfield (44-10-2) vs Oleksandr Usyk (18-0)

Oleksandr Usyk vs Evander Holyfield makes for an interesting matchup because both men’s careers have played out in similar ways. Evander Holyfield is the only fighter in boxing history to become undisputed champion in two different weight classes doing so in the cruiserweight and heavyweight division. His resume of wins is Dwight Muhammad Qawi, Carlos De Leon, James “Buster” Douglas, George Foreman, Larry Holmes, Riddick Bowe, Mike Tyson and Michael Moorer. His combination of power and heart made him a tough outing for anyone who stepped in the ring with him. Like Evander Holyfield, Oleksandr Usyk also became undisputed champion in the cruiserweight division in 2018 while also winning the World Boxing Super Series. This makes him the only undisputed cruiserweight champion in the four belt era. Usyk has only had two fights at heavyweight so far but he is in place to have great success in the division. Holyfield vs Usyk not only has a great storyline but they are similar in that they are unpredictable able to win a fight in many different ways.

Roy Jones Jr. (66-9) vs Canelo Alvarez (55-1-2)

While Canelo Alvarez is arguably the biggest star in boxing today, Roy Jones Jr. was arguably the biggest star in boxing throughout the 90s. In his prime, Roy Jones Jr. reigned as pound-for-pound king winning world championships at middleweight, super middleweight, light heavyweight and heavyweight. His impressive resume of wins includes Bernard Hopkins, James Toney, Mike McCallum, Montell Griffin, Virgil Hill, Antonio Tarver and Felix Trinidad. Meanwhile, Canelo Alvarez is the current pound-for-pound king currently reigning as unified super middleweight champion. In addition, he has also won world championships in the super welterweight, middleweight and light heavyweight. He also has an impressive resume that features Shane Mosley, Miguel Cotto, Amir Khan, Gennadiy Golovkin, Daniel Jacobs, Sergey Kovalev and Callum Smith. This would be an excellent tactical fight as both men have similar styles where they excel as defensive fighters but can also destroy their opponents with their power and their arsenal of punch combinations.

Manny Pacquiao (62-7-2) vs Julio Cesar Chavez (107-6-2)

Manny Pacquiao and Julio Cesar Chavez are two of the most decorated fighters in the history of boxing. Manny Pacquiao has won world championships in eight weight classes more than any fighter in boxing’s storied history. He has beaten a total of 25 former or future world champions in his career and has 17 wins in world title fights. Meanwhile, in a sport with deep Mexican roots, Julio Cesar Chavez has a claim of being the greatest of them all. His career began with one of the greatest win streaks in boxing history as it took him 87 fights before he suffered his first professional loss. Chavez won world championships in three weight classes and beat 18 world champions in his career. Of all the fights on this list, this for sure would be the favorite to be the most exciting. Both men are known for being in some of the most exciting fights in boxing history with their willingness to trade punches with their opponents in the middle of the ring. Not only that, but both men are extremely tough as they have only been stopped a combined seven times in 186 total fights so either of them getting a stoppage in this fight would be unlikely.

Mike Tyson (50-6) vs Deontay Wilder (42-1-1)

Deontay Wilder and Mike Tyson are two of the most powerful fighters in boxing history. Deontay Wilder has finished all but two of his opponents in his career by knockout with 20 coming in the first round. He reigned as WBC Heavyweight champion for five years successfully defending his title 10 times winning each fight by knockout. Meanwhile, Mike Tyson turned pro at 18-years-old and quickly made a name for himself finishing his opponents with highlight reel knockouts. Over one year later, Tyson became the youngest world heavyweight champion in boxing history when he beat Trevor Berbrick via 2nd round KO. In 1987, he became undisputed heavyweight champion a title that he would hold for over two years. Trust and believe this will not go the full 12 rounds as one of these fighters is sure to hit the canvas in spectacular fashion. That’s what makes this matchup so exciting both of these men are not only powerful, but they are relentless and will do whatever it takes to close the show.

Tyson Fury (30-0-1) vs Muhammad Ali (56-5)

Muhammad Ali is widely regarded as the greatest pound-for-pound fighter the sport of boxing has ever seen. His amazing footwork, power, defensive technique, and showboating made him adored by boxing fans around the world. Ali beat some of the greatest heavyweights in boxing history including George Foreman, Joe Frazier, Sonny Liston, Ron Lyle and Ken Norton. Die hard boxing fans would say it’s blasphemous to compare anyone, let alone another fighter, to the great Muhammad Ali. While they are right no one compares to Ali, I can’t deny that a fight between him and Tyson Fury would be very entertaining. Like Ali, current WBC Heavyweight champion Tyson Fury also has great footwork and defense but does it with a much bigger frame than Ali. He is also very quick for a guy his size able to put together quick boxing combinations and dodging oncoming attacks from his opponent. This would not only be a fun fight to see from a skill standpoint, but also from an entertainment standpoint as both men are two of the most flamboyant fighters the sport of boxing has ever seen. Also, sidebar but this would make for the best press conference as both men do not bite their tongue and will trash talk each other the entire time.

Sugar Ray Leonard (36-3-1) vs Floyd Mayweather (50-0)

Ok so this may be cheating because Floyd Mayweather is no longer active. However, Floyd had such a great career its only right he be included in this. Floyd finished his career a perfect 50-0 winning world championships in five different weight classes. His resume of wins is extraordinary including Jose Luis Castillo, Arturo Gatti, Zab Judah, Oscar De La Hoya, Ricky Hatton, Juan Manuel Marquez, Shane Mosley, Miguel Cotto, Canelo Alvarez and Manny Pacquiao. While he made his name as a brawler beating his opponents using an aggressive offensive style to defeat his opponents, he became a star as a defensive fighter beating his opponents using his intelligence and quickness to frustrate. One name that has always been linked to Floyd in terms of dream fights is another one of boxing’s all-time greats “Sugar” Ray Leonard. Sugar Ray Leonard ruled over the sport of boxing in the 1980s also winning world titles in five weight classes. He has an impressive resume of his own securing wins against Wilfred Benitez, Roberto Duran, Thomas Hearns, Marvin Hagler, and Donny Lalonde. Leonard was well-known for his quick hands able to get off quick combinations against his opponents at an instant and his amazing footwork. This matchup would be a showcase of technical boxing at its finest and is sure to be highly entertaining.