Boxing has always been a sport full of excitement, skill, and unforgettable moments.
Over the years, some matches have become more than just fights—they have turned into worldwide events that broke records and brought in huge amounts of money.
These matches featured some of the greatest fighters in history, with intense rivalries and thrilling stories that captured the attention of millions
From Floyd Mayweather’s clever strategies to Mike Tyson’s unmatched power, and from the highly anticipated Mayweather vs. Pacquiao fight to the famous Tyson vs. Holyfield battles, these matches not only shaped the careers of the fighters but also changed the sport forever.
They showed just how popular boxing could be, with fighters earning massive sums of money and matches breaking revenue records.
This article takes a closer look at some of the most memorable boxing matches in history, where the fighters walked away with jaw-dropping paychecks.
| Match | Total Revenue | Athlete 1 Earnings | Athlete 2 Earnings |
|---|---|---|---|
| Floyd Mayweather Jr. vs. Manny Pacquiao (May 2, 2015) | Approximately $600 million | Mayweather: $250 million | Pacquiao: $150 million |
| Floyd Mayweather Jr. vs. Conor McGregor (August 26, 2017) | Approximately $550 million | Mayweather: $275 million | McGregor: $85 million |
| Floyd Mayweather Jr. vs. Saul “Canelo” Alvarez (September 14, 2013) | Approximately $150 million | Mayweather: $75 million | Alvarez: $12 million |
| Oscar De La Hoya vs. Floyd Mayweather Jr. (May 5, 2007) | Approximately $136 million | De La Hoya: $52 million | Mayweather: $25 million |
| Evander Holyfield vs. Mike Tyson II (June 28, 1997) | Approximately $100 million | Holyfield: $35 million | Tyson: $30 million |
| Lennox Lewis vs. Mike Tyson (June 8, 2002) | Approximately $112 million | Lewis: $30 million | Tyson: $30 million |
| Mike Tyson vs. Peter McNeeley (August 19, 1995) | Approximately $96 million | Tyson: $25 million | McNeeley: $540,000 |
| Floyd Mayweather Jr. vs. Miguel Cotto (May 5, 2012) | Approximately $94 million | Mayweather: $45 million | Cotto: $8 million |
| Mike Tyson vs. Roy Jones Jr. (November 28, 2020) | Approximately $80 million | Tyson: $10 million | Jones Jr.: $3 million |
| Evander Holyfield vs. George Foreman (April 19, 1991) | Approximately $80 million | Holyfield: $20 million | Foreman: $12 million |
| Floyd Mayweather Jr. vs. Shane Mosley (May 1, 2010) | Approximately $78.3 million | Mayweather: $40 million | Mosley: $6.7 million |
| Floyd Mayweather Jr. vs. Juan Manuel Marquez (September 19, 2009) | Approximately $70 million | Mayweather: $25 million | Marquez: $3.2 million |
| Mike Tyson vs. Evander Holyfield I (November 9, 1996) | Approximately $77.9 million | Tyson: $30 million | Holyfield: $12 million |
| Floyd Mayweather Jr. vs. Robert Guerrero (May 4, 2013) | Approximately $60 million | Mayweather: $32 million | Guerrero: $3 million |
| Oscar De La Hoya vs. Felix Trinidad (September 18, 1999) | Approximately $70 million | De La Hoya: $21 million | Trinidad: $8.5 million |
Floyd Mayweather Jr. vs. Manny Pacquiao (2015)
Held at the MGM Grand in Las Vegas, this fight was hyped as the “Fight of the Century” and became one of the most financially successful events in sports history.
Fans around the world tuned in to watch two of the greatest fighters of their generation face off. The event generated enormous revenue, breaking records for pay-per-view sales.
Inside the ring, Mayweather’s defensive skills and tactical approach allowed him to outpoint Pacquiao over 12 rounds. Pacquiao later revealed he had been dealing with a shoulder injury, which frustrated many fans expecting a more action-packed fight.
Despite the criticism, Mayweather won by unanimous decision and maintained his unbeaten record.
Floyd Mayweather Jr. vs. Conor McGregor (2017)
The fight between Mayweather and McGregor at the T-Mobile Arena in Las Vegas was one of the most unusual events in boxing history.
McGregor, an MMA champion, made his boxing debut, stepping into a completely new arena. The buildup was filled with trash talk and global attention, making it a massive crossover event.
Despite McGregor’s early aggression, Mayweather’s experience and endurance proved too much.
Mayweather employed a patient strategy, wearing McGregor down before securing a TKO victory in the 10th round. The fight became one of the richest in history, with Mayweather earning an estimated $275 million.
Floyd Mayweather Jr. vs. Saul “Canelo” Alvarez (2013)
At the MGM Grand in Las Vegas, Mayweather faced a young and powerful Canelo Alvarez, who was undefeated at the time.
Many believed this would be one of Mayweather’s toughest tests, as Canelo had the power and size advantage.
However, Mayweather delivered a boxing masterclass, using his speed, movement, and precision to completely outbox Canelo.
The fight ended in a majority decision in favor of Mayweather, with one judge controversially scoring it a draw. This victory demonstrated Mayweather’s dominance, even against younger opponents.
Oscar De La Hoya vs. Floyd Mayweather Jr. (2007)
This fight at the MGM Grand in Las Vegas was one of the most anticipated of the decade, as two of the biggest names in boxing clashed.
De La Hoya, the bigger fighter, used his size advantage to try to control the early rounds.
However, Mayweather’s defense and counterpunching took over in the second half of the fight.
The bout ended with Mayweather winning by split decision, which some fans felt could have gone either way. The victory boosted Mayweather’s career and solidified his nickname, “The Best Ever.”
Evander Holyfield vs. Mike Tyson II (1997)
Known as the “Bite Fight,” this rematch at the MGM Grand in Las Vegas was one of the most controversial events in sports history.
Tyson, seeking redemption after losing their first fight, entered the ring aggressively.
In the third round, Tyson bit Holyfield’s ear not once but twice, causing the referee to disqualify him.
The shocking moment left fans stunned and damaged Tyson’s reputation. Holyfield remained calm and walked away with the victory.
Lennox Lewis vs. Mike Tyson (2002)
This fight, held at the Pyramid Arena in Memphis, was a battle between two heavyweights with different styles. Tyson, known for his explosive power, came out aggressively in the early rounds.
Lewis used his reach, size, and technical skills to dominate the fight. In the 8th round, Lewis knocked Tyson out with a thunderous punch, cementing his status as one of the best heavyweights of all time.
Mike Tyson vs. Peter McNeeley (1995)
Tyson’s return to the ring after serving time in prison was a major event, with fans eager to see if he could still dominate. The fight, held at the MGM Grand in Las Vegas, was heavily promoted.
McNeeley entered the ring with energy but was quickly overpowered by Tyson. The fight lasted less than two minutes before McNeeley’s corner threw in the towel, marking Tyson’s triumphant comeback.
Floyd Mayweather Jr. vs. Miguel Cotto (2012)
At the MGM Grand in Las Vegas, Cotto gave Mayweather one of the toughest fights of his career.
Cotto’s aggressive style and power punches challenged Mayweather in ways few fighters had before.
Despite Cotto’s efforts, Mayweather’s precision and ring intelligence allowed him to win by unanimous decision.
The fight was praised for its intensity, with Mayweather later calling Cotto one of his toughest opponents.
Mike Tyson vs. Roy Jones Jr. (2020)
This exhibition fight at the Staples Center in Los Angeles brought two legends back into the ring. Both Tyson and Jones showed glimpses of their former greatness, despite their age.
The fight ended in a draw, with no official winner declared.
Fans appreciated the nostalgic event and praised both fighters for their efforts, showing their love for the sport even after retirement.
Evander Holyfield vs. George Foreman (1991)
This clash between Holyfield and Foreman in Atlantic City was a battle of youth versus experience. Foreman, known for his knockout power, tried to use his size to his advantage.
Holyfield, however, outlasted Foreman with superior speed and stamina, winning by unanimous decision.
Despite the loss, Foreman’s toughness impressed the crowd as he went all 12 rounds.
Floyd Mayweather Jr. vs. Shane Mosley (2010)
Mosley shocked Mayweather early in the fight at the MGM Grand in Las Vegas, landing a big punch that momentarily wobbled Mayweather. However, Mayweather quickly regained control of the fight.
From that point onward, Mayweather’s precision and defense dominated Mosley.
He won easily by unanimous decision, showcasing his ability to adapt to tough moments.
Floyd Mayweather Jr. vs. Juan Manuel Marquez (2009)
Mayweather’s return after a long break was a highly anticipated event at the MGM Grand in Las Vegas. Marquez, though an excellent fighter, was clearly outmatched.
Mayweather’s dominance was on full display, winning every round with ease. This fight marked the beginning of Mayweather’s highly lucrative comeback.
Mike Tyson vs. Evander Holyfield I (1996)
Holyfield shocked the world in this Las Vegas clash by standing up to Tyson’s power. He used his own strength and resilience to frustrate Tyson.
The fight ended in an 11th-round TKO, with Holyfield becoming the heavyweight champion. It was a career-defining moment for Holyfield.
Floyd Mayweather Jr. vs. Robert Guerrero (2013)
At the MGM Grand in Las Vegas, Mayweather put on a boxing clinic, easily outclassing Guerrero. His defense and speed were too much for his opponent.
The fight ended with a unanimous decision for Mayweather, who remained undefeated and showcased his dominance in the ring.
Oscar De La Hoya vs. Felix Trinidad (1999)
This fight at the Mandalay Bay in Las Vegas was one of the most controversial of its time. De La Hoya dominated the early rounds with superior technique and speed.
However, he slowed down in the later rounds, which allowed Trinidad to win a majority decision. Many fans and analysts believed De La Hoya deserved the victory.