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5 Biggest Floyd Mayweather Career Moments

Reliving Floyd Mayweather's Toughest Challenge in the Ring


5 Biggest Floyd Mayweather Career Moments

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5 Biggest Floyd Mayweather Career Moments

Floyd Mayweather Jr. is considered by many to be the greatest boxer of all time. For 26 years, he dominated the World Boxing Association (WBA) and went undefeated with 50 wins, of which 27 were knockouts and 23 he won via decision.

He’s had an amazingly successful career with epic moments where he made his mark in boxing history, and here are 5 of the biggest ones.

The First and Last Loss


1. Serafim Todorov loss

As an amateur boxer, Mayweather competed in the 1996 Olympics and won a bronze medal in the featherweight division. He lost to Bulgarian Serafim Todorov, the last man to beat Mayweather on record in a boxing ring. After experiencing the disappointing loss, instead of giving up, Mayweather was inspired to train as hard as he could and dedicate himself to winning. He knew that he never wanted to experience the losing feeling again. The loss was probably the best thing that happened to him, as it prepared him to fight to win.

The New King of Boxing

2. Oscar De La Hoya win

In May 2007, Mayweather took on the “Golden Boy” for the World Boxing Council (WBC) light-middleweight title. This was the last time Mayweather entered the ring and wasn’t the “A-side.” De La Hoya was the favored pick for this fight, but they were wrong! Mayweather took the world by storm and beat De La Hoya via split decision, and immediately took over as the new king of boxing. This win proved to the world that Mayweather has what it takes to seek and destroy any challenger that’s in his way, even if they’ve won 10 world titles.

3. Manny Pacquiao win

There are not that many names out there that could compete with Mayweather except for Manny Pacquiao. Even though Mayweather was defeating legends, so was Manny Pacquiao, as they were both at the peak of their careers at the same time. When it came to these two fighters, the only question was, when will they meet in the ring? On May 2, 2015, the showdown finally arrived, and it came to be known as the “Fight of The Century.” Mayweather outperformed Pacquiao and won the fight by unanimous decision!

4. Conor McGregor win

On August 26, 2017, Mayweather went into the ring against Conor McGregor, a former Ultimate Fighting Championship (UFC) champion. McGregor was famous in UFC for his punching power, but when he went up against Mayweather, his striking wasn’t on the same level. Mayweather defeated McGregor by technical knockout (TKO) in the 10th round and extended his professional boxing record to 50 wins and 0 losses.

Life After Boxing

5. Logan Paul win

On August 26, 2017, Mayweather retired from professional boxing. However, he has actually retired multiple times starting in 2007. Whilst life after competitive sports can be perilously tough, he made the most of his first hiatus from boxing by appearing in the World Wrestling Entertainment (WWE) in a fight against Big Show. On June 6, 2021, Mayweather also got back into the ring with YouTuber Logan Paul for an exhibition boxing match. They went the eight-round distance, but it was obvious that Mayweather never exerted himself beyond warm-up mode. He kept it entertaining for the spectators and gave them a show.

It was estimated that the exhibition generated $50 million. According to, Mayweather received a base of $10 million just for participating, as well as a 50 percent pay-per-view share. If you do the math, it’s no wonder why Mayweather’s nickname is “Money,” as he sure knows how to make it, even after retirement! Pro sports might be tough when many athletes leave, but for Mayweather, it was just another opportunity.

On June 12, 2022, Floyd Mayweather, Jr. was given one of the highest and most prestigious honors in sports – he was inducted into the International Boxing Hall of Fame! He has had many great moments throughout his victorious career, and these are the best ones in our book. But, the book is not yet written, and there are loads more to look forward to, like awesome fights such as exhibition matches.

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Michael is the CEO of Last Word On Sports INC and is happy to be involved with Big Fight Weekend. He is credentialed with several international governing bodies. He cites the Hagler-Leonard fight as his introduction to boxing--and what an introduction that was!

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