Floyd Mayweather Jr took the boxing world by storm throughout his outstanding professional career.

He entered the paid ranks in the back end of 1996, just a few months after he captured an Olympic Gold Medal at the Summer games in Atlanta of the same year.

‘Money’ won 15 major world titles across five weight classes during his tenure, ranging from super-featherweight all the way through to light-middleweight.

He holds legacy-defining victories over a number of generational greats, defeating the likes of Oscar De La Hoya, Canelo Alvarez and Manny Pacquiao, locking horns with the latter in the ‘Fight Of The Century’ back in 2015.

After his victory over Conor McGregor in their monumental crossover match-up in August 2017, Mayweather announced his retirement from boxing shortly after, walking away from the sport with a perfect unbeaten record of 50-0.

Despite this, legendary trainer Freddie Roach believes ‘Money’ did not deserve to draw the curtain on his career without a loss, claiming the retired pound-for-pound star lost one fight in particular.

In an interview Roach claimed ‘Money’ should have tasted defeat in his career when he fought Jose Luis Castillo for the first time.

“Floyd can say what he wants, but I saw Floyd get almost beat by Oscar and when he fought [Jose Luis] Castillo for the first time.

I thought Castillo won their first fight. He put pressure on Floyd and broke him down.”

Mayweather faced Castillo on two occasions during 2002, winning both of these bouts via unanimous decision although it has been argued that the former Mexican star should have had his hand raised in their controversial first bout.