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The 10 Biggest Boxing Matches of All Time

10 Biggest boxing matches!

Mike Goodpaster

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Publish Date: 12/18/2022

Fact checked by: Simon Briffa

Today I will look at what I believe are the ten biggest fights in the history of boxing. When considering the “biggest” fights, I place a lot of weight on whether the fight is transcendent, historical and socially significant. Yes, Mayweather-Pacquiao is certainly transcendent, but I believe the other two criteria are lacking. Let’s face it: If this matchup took place in 2010, it would most certainly place in the top 5. While both fighters are still top 10 Pound for Pound, they are no longer 1-2. Mayweather looked mortal in his last two fights and just two years ago, Pacquiao was knocked out cold. What follows are, in my view, the top 10 significant (not necessarily the best) fights in boxing history: Check out the Boxing odds for betting on boxing.

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10. Floyd Mayweather – Manny Pacquiao

Still a tremendous and highly anticipated match-up but still a few years too late, which was proven by the lack of action during the fight. It will still be the highest-grossing fight in history but falls short in historical significance because it should have taken place 5 years ago.

Floyd Mayweather vs Manny Pacquiao Full Fight Highlights

9. Sugar Ray Leonard – Roberto Duran I

The classic matchup, classic fight! You had the darling of the American media and 1976 Olympic Gold Medalist in Leonard and the surly angry Duran who had tasted defeat only once in his Hall of Fame career. At the time, it was the richest-grossing non-heavyweight fight in boxing history. Leonard was a champion with cross-over appeal, and Duran was a fight fan’s fighter. The fight exceeded expectations as Leonard surprised everybody by standing flat-footed and fighting Duran’s fight. Duran won a very close decision, and Leonard won the respect of everyone who thought he was a media creation.

Duran vs Leonard I | Brawl in Montreal | Great Fight Highlights 🎥✨

8. Sugar Ray Leonard – Marvin Hagler

A long-awaited matchup that people had wanted to see as early as 1982. Unfortunately, Leonard retired after suffering a detached retina. Leonard had fought only Kevin Howard in a short-lived comeback fight in 1984 before retiring again. In late 1986, Leonard decided to return and wanted to fight Hagler. Hagler had been a very active fighter since 1982 and had engaged in many wars. Leonard saw this as the perfect time to get Hagler in the ring. Hagler’s last fight before Leonard was a brutal fight with John “The Beast” Mugabi. Leonard entered the fight as a decided underdog but, using his extraordinary foot speed easily won the first four rounds. Hagler slowly started applying more pressure and was the aggressor over the last eight rounds. Leonard fought in spurts for the rest of the fight and, in the judges’ eyes, did enough to earn a split-decision victory.

“Marvelous” Marvin Hagler vs “Sugar” Ray Leonard (highlights)

7. Sugar Ray Leonard – Thomas “Hit Man” Hearns I

A highly anticipated fight that pitted Hearns, an undefeated power puncher from Detroit, Michigan, against the media darling Ray Leonard. Leonard had proven himself an all-time great at a very young age with his wins over Wilfred Benitez and his rematch win over Roberto Duran. Hearns, on the other hand, was more of a mystery. He had destroyed Pipino Cuevas in two devastating rounds the year before, but there were still questions about his legitimacy. During the first four rounds, there wasn’t much action, but a see-saw battle ensued at the start of the fifth round. Hearns surprisingly outboxed the boxer in the majority of the later rounds and was leading on all scorecards entering the 14th round. When Leonard came out for the round with his eye swollen, he somehow reached down and staged one final assault stopping Hearns in a truly memorable fight.

Sugar Ray Leonard vs Thomas Hearns 1 Full HIGHLIGHTS

6. Larry Holmes – Gerry Cooney

This is a fight that had huge racial undertones. Gerry Cooney was a modern-day “White Hope” who was slowly taken to the top, fighting no top contenders. Prior to this fight, Cooney fought past their prime former contenders such as Ken Norton, Jimmy Young and Ron Lyle. Cooney’s devastating punching power made him an easy sell. This, combined with the color of his skin, made Cooney the perfect heavyweight. Larry Holmes was the undefeated African-American champion who got little respect following the legendary Muhammad Ali. Cooney, the challenger, was on the cover of Sports Illustrated and even made the cover of Time magazine, while Holmes was widely ignored. Cooney got purse parity with Holmes which was unheard of for a challenger and when they got into the ring was announced last, an honor usually reserved for the champion. A brutal grueling struggle ensued with Holmes flooring Cooney in the second round. Cooney had his moments but was eventually worn down and outclassed by the champion. Victor Valle Cooney’s trainer rescued the challenger in the 13th round.

Larry Holmes vs Gerry Cooney – Highlights (The PRIDE & The GLORY)

5. Muhammad Ali – George Foreman

Known as the “Rumble in the Jungle”, this is the fight that took Ali to superhero status worldwide. Foreman had easily disposed of Ken Norton and Joe Frazier, two fighters who had given Ali all he could handle. Largely because of this, most considered Ali’s chances to be little to none. Foreman was a thunderous puncher who had never been taken deep into a fight, Ali laid on the ropes for most of the first seven rounds of the fight, fighting only in spurts. In the eighth round, Ali opened up with a multiple-punch combination that finally drove Foreman to the canvas towards the end of round eight. Foreman, beaten up and totally fatigued, was counted out at the end of the round.

Muhammad Ali vs George Foreman (Highlights) The Rumble In The Jungle

4. Gene Tunney – Jack Dempsey II

The “Long Count” fight transcended boxing mainly because of Jack Dempsey. Dempsey reached truly iconic stature in the 1920s worldwide. Tunney was the former Light Heavyweight Champion who had shocked the world by winning an easy decision in their first fight. Tunney was the underdog in the second fight, as well as the public, couldn’t imagine Dempsey losing again. The second fight was closer, but Tunney still controlled the fight until the seventh round when Dempsey made a fatal mistake. After flooring Tunney, he stood over him, preventing the referee from counting Tunney out. The fight that took place at Soldier Field in Chicago and Illinois had recently changed the rule to mandate the count couldn’t start until the fighter had moved to a neutral corner. Dempsey had obviously forgotten the rule change, which cost him a chance to reclaim his belt. Tunney regained his composure and won a decision.

Jack Dempsey vs Gene Tunney – The Long Count (1927)

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3. Jack Johnson – James Jeffries

July 4th, 1910, was the date of the very first “Fight of the Century” which pitted the first African-American heavyweight champion against the former undefeated White heavyweight champion. After Jeffries retired, the heavyweight champions over the next few years left a lot to be desired (Marvin Hart and Tommy Burns). Jack Johnson dominated Burns in eight rounds in 1908 and White America’s search for a “Great White Hope” was on. James Jeffries, overweight and hadn’t fought in six years, was pulled reluctantly off his farm to fight Johnson. What ensued with this fight was one of the genuinely shameful occurrences in our country’s history. Johnson toyed with and ultimately destroyed Jeffries, triggering riots and even death. All because a black man proved the color of his skin did not make him inferior. Check out the boxing betting sites for betting on boxing.

DBBH – Jack Johnson -vs- Jim Jeffries (July 4th, 1910)

2. Joe Louis – Max Schmeling II

This fight was genuinely transcendent and had huge historical and social significance. Joe Louis was the American champion defending his title against Max Schmeling, a native German who was considered a Nazi even though he had a Jewish manager in Joe Jacobs. What added to the drama and anticipation of this fight was the fact that they had fought two years earlier before Louis was a champion, and Schmeling had beaten Louis senseless. The rematch would occur on June 1938 at legendary Yankee Stadium in front of 77,000 people, including many dignitaries. Louis destroyed Schmeling in the first round. The beating was so bad that Louis literally broke Schmeling’s neck, and the Nazi broadcast back to Germany was stopped before the first-round knockout. Schmeling and Louis later in life became great friends, and Schmeling even helped pay some of Joe’s medical costs later in life.

Joe Louis vs. Max Schmeling 2 | Full HD

1. Joe Frazier – Muhammad Ali I

Billed as “The Fight”, it took place on a Monday night at Madison Square Garden in New York before a star-studded crowd. (Tickets were so challenging to come by that Frank Sinatra could only gain entry as a ringside photographer!) Ali had gotten his boxing license back just five months earlier after being away from the sport for three and a half years and had quickly beaten contenders Jerry Quarry and Oscar Bonavena. The fight was rushed for fear that Ali would soon be going to jail because of his refusal to enter the military draft for the Vietnam War. Frazier was considered the “White” establishment fighter, while Ali was the Black Muslim fighter. The fight lived up to its billing. Ali started fast and controlled the early action, but Frazier was slowly starting to get inside Ali’s jab, breaking Ali down with his sledgehammer left hook. The fight was a close affair, with the defining moment coming in the 15th round when Frazier landed a huge left hook that put Ali on the canvas. Frazier went on to win a unanimous decision on a truly historic night.