Floyd Mayweather faced a great deal of opposition throughout his career, from Manny Pacquiao to Ricky Hatton, but one of his toughest tests came at the hands of a far lesser-known boxer.
Floyd Mayweather, who retired in 2017 with a perfect record of 50-0, has had more than his fair share of challenges, from the time Marcos Maidana knocked out ‘Money’ Mayweather’s tooth and wore it as a necklace, to his close shave with Jose Luis Castillo.
Mayweather has since fought the likes of Logan Paul and John Gotti III in exhibition matches, though fans have wondered why Mayweather continues exhibition fights after the wealth he’s already gained from the sport.
The boxing icon has been involved in some of the biggest PPV fights in the history of the sport, but one of his toughest tests comes at the hands of a 38-34 journeyman, known as ‘The Drunken Master’.

Emanuel Augustus made Floyd Mayweather ‘dig deep’
The pair met in the ring in 2000, when Mayweather held a record of 23-0, and Augustus a deceptive record of 22-16-4.
Augustus would give Mayweather trouble in the fight, with Mayweather visibly bleeding from the nose during their encounter. Despite this, Mayweather would go on to stop Augustus in the ninth round.
After the fight was over, Mayweather told his corner ‘he’s a tough m———–. I had to dig deep’, before singing his praises in the post-fight press conference, labeling Augustus ‘a true warrior a true champion’.

In 2012 Mayweather told Fight Hub TV that ‘Emanuel Augustus was my toughest opponent thus far and his record didn’t show his skillset, but the guy was unbelievable’. Mayweather has since claimed Pacquiao was his toughest test.
Augustus holds the nickname of ‘Drunken Master’ due to his strange and orthodox style of boxing. His movement is like no other boxer, throwing shots from a variety of unexpected angles and moving in a way that has been compared to a puppet on a string.
The night Emanuel Augustus gave Micky Ward a run for his money
In 2001, in his third fight since facing Mayweather, Augustus took on Irishman Micky Ward.
Ward was only two fights removed from the start of his thrilling trilogy with Arturo Gatti, and held a record at the time of 36-10. Augustus meanwhile took the fight with a record of 24-17-4.
The fight was a blockbuster battle that saw constant back-and-forth between the two, though Ward eventually got to Augustus with a left hook to the body in the ninth round.

Ward would go on to win a close decision, with one scorecard reading 96-94, though many fans believe Augustus could have rightly got the nod.
The fight was voted Ring Magazine’s Fight of The Year in 2001, and is just another testament to the skillset of Emanuel Augustus.