In Floyd Mayweather’s career, he never lost a single fight. That’s not to say he didn’t come close to losing on several occasions. Throughout his boxing career, however, he managed to pull off one victory after another against the likes of Manny Pacquiao, Oscar De La Hoya, Shane Mosley, and many others. Surprisingly, Mayweather doesn’t consider any of those big names his toughest opponent.

Floyd Mayweather’s toughest fights

It all started back in 1996. That’s when Floyd Mayweather won his first professional bout over Roberto Apodaca. It was the first of many. Two years later, Mayweather won his first belt, the WBC super featherweight title. 

In his career, which finally ended in 2017, Mayweather fought to a perfect 50-0 record. While his record is unblemished, it didn’t come without some bumps along the way. 

Despite never having lost a fight in 50 attempts, Mayweather hasn’t always been dominant. Oscar De La Hoya was the first fighter to pose any serious threat to Mayweather’s reign in 2007. During that fight, De La Hoya never backed down from Mayweather and at the halfway point the scorecard was even. Mayweather, however, finished strong and won by a majority decision.

Canelo Alverez and Marcos Maidana also challenged Mayweather. In each case, Mayweather earned a majority decision. Many boxing pundits believe the closest Mayweather ever came to defeat came at the hands of Jose Luis Castillo in April 2002. The crowd and many others thought Castillo had upended the champ. The judges disagreed.

Mayweather said Emanuel Augustus was tough

Early in his career in 2001, Mayweather took his 24-0 record against a relatively unknown fighter named Emanuel Augustus, who had a 22-16-4 record. Augustus, whose nickname was the Drunken Master because his style appeared to be part boxer, part string-puppet, gave Mayweather a much tougher fight than expected. 

Mayweather dominated early, but the underdog responded in the fifth with a flurry of punches that bloodied Mayweather’s nose and brought the crowd to its feet. Mayweather recovered and took control during the later rounds. He won in the ninth when Augustus’s corner threw in the towel. In the post-fight interview, Mayweather talked about his opponent.

“He’s a true warrior, a true champion. Before the fight, I heard he had got robbed [via poor judging decisions] a lot of times – and I believe that’s true.”

Floyd Mayweather said Miguel Cotto was toughest he ever faced

In May 2012, Floyd Mayweather faced off against Miguel Cotto in a WBA Super Light Middleweight title fight in Las Vegas. Cotto entered the fight with a 37-2 record while Mayweather’s record stood at 42-0. 

Much like the Augustus fight, Mayweather started strong, but then the challenger responded and bloodied up Mayweather’s nose in both the fourth and fifth rounds. The champ recovered and took control until the eighth, when Cotto pushed Mayweather into a corner and delivered a healthy dose of combinations to the head and body. 

Mayweather was battered and bloodied throughout much of the fight, and despite being physically pushed hard late into a fight, which was a rarity, he endured Cotto’s onslaught of punches and came out with a convincing victory on all of the judge’s scorecards. Mayweather said the Cotto fight was, without question, the most difficult challenge of his career.

“Emanuel Augustus was tough. Miguel Cotto was tougher. Miguel Cotto was the toughest fighter I’ve faced thus far,” Mayweather said in a post-fight interview. “He tried to come on stronger in the later rounds, which made me fight harder. He brought out the best in Floyd Mayweather.”

Following the Cotto fight, Mayweather went on to win seven more times before retiring in 2017. He always maintained Cotto was his toughest opponent. Years later, Cotto reciprocated, saying Mayweather was his toughest fight ever.