Ranking Floyd Mayweather Jr’s 5 toughest career fights

Floyd Mayweather
Unbeaten
Defensive specialist
Exhibition fights
People forget
Toughest fights
Emanuel Augustus, 2000 (5)
‘Emanuel Augustus first’
Shane Mosley, 2010 (4)
Knockout power
Oscar De La Hoya, 2007 (3)
Too fast
Marcus Maidana, 2014 (2)
Doing what he needed to do
Miguel Cotto, 2012 (1)
Drawing blood
Floyd Mayweather

Floyd 'Money' Mayweather Jr is arguably the greatest boxer of all time, who fought in the welterweight division from 1996-2017.

Unbeaten

In his 21-year boxing career, Mayweather won all 50 of his fights, including 27 knockout victories and 15 title victories.

Defensive specialist

Mayweather developed and is famed for his defensive style, perfecting the 'hit and not get hit' approach to boxing.

Exhibition fights

The 46-year-old now fights in exhibition fights with celebrities and YouTubers, with the most famous match-up being against internet sensation and WWE star Logan Paul.

People forget

The way Mayweather's career has turned, people tend to forget how good of a boxer Floyd 'Money' Mayweather was.

Toughest fights

Here are Floyd Mayweather Jr's five toughest victories in his professional boxing career.

Emanuel Augustus, 2000 (5)

Mayweather fought the 'Drunken Master' Augustus in what he confessed was his hardest fight. Augustus was a boxer known for poor preparation, but he was ready for Mayweather. His Unorthodox style gave 'Money' problems, but he came out on top with a points decision victory.

‘Emanuel Augustus first’

According to thesun.co.uk, Mayweather said, "If I was rating certain fighters out of every guy that I fought, I'm going to rate Emanuel Augustus first compared to all the guys that I've faced."

Shane Mosley, 2010 (4)

The closest Floyd Mayweather got to being knocked out was in 2010 against 'Sugar' Shane Mosley at the MGM Grand in Las Vegas.

Knockout power

Mosley earned 41 of his 49 career wins by knockout and tested Mayweather, catching with two devastating rights hand in the second round, causing his knees to buckle. However, Mayweather held on and secured the victory later in the fight.

Oscar De La Hoya, 2007 (3)

Mayweather stepped up to light-middleweight for his fight against the 'Golden Boy' Oscar De La Hoya.

Too fast

De La Hoya used his size and weight to his advantage in the early rounds of the fight. Despite that, Mayweather capitalized on his heavier opponent, proving too fast and accurate for the 'Golden boy.' One judge did give De La Hoya the fight, making it his only split-decision win.

Marcus Maidana, 2014 (2)

The first fight between Maidana and Mayweather was one of his toughest matchups, with the Argentinian relying on strength and aggression to keep the champion against the ropes to absorb ferocious overhand shots.

Doing what he needed to do

Mayweather was actively counterpunching Maidana, keeping in favor with judges. At the end of the fight, Mayweather won by the decision but took nothing to chance and dominated Maidana in a rematch later in the year.

Miguel Cotto, 2012 (1)

Floyd Mayweather's fight against Miguel Cotto was the hardest fight of his career. Cotto utilized his jab and made it hard for Mayweather to get into a rhythm in the fight.

Drawing blood

Cotto's punches hit Mayweather flush, causing 'Pretty Boy' to draw blood which never really happened in his previous fights. According to sportskeeda.com, Mayweather said, "Miguel Cotto was the toughest fighter that I've faced thus far."

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