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Who Wins In Leonard – Mayweather, Ali – Louis? 

What would happen if it were ‘Sugar’ Ray Leonard fighting Floyd ‘Money’ Mayweather, Jr.?

Sugar Ray Leonard won the Olympic Gold medal in 1976 at Montreal, Canada. He ended his amateur career with a final record of 145-5.  Floyd Mayweather won the Olympic Bronze medal in 1996 in Atlanta, Georgia; his final amateur record was 84-9.

Leonard won the WBC Welterweight title, defeating Wildred Benitez, 38-0-1, in November of 1979. At 27-0, he lost to Roberto ‘Hands of Stone’ Duran, 71-1. In the rematch, he stopped Duran in 8 rounds.

Three fights later in 1981 behind he stopped WBA champion Thomas ‘Hit Man’ Hearns, 32-0, in the 14th round.  After winning his next fight, he had to recover from a detached retina, stopping Kevin Howard, 20-4-1, in 9 rounds.

Three years later, he returned to the ring, defeating WBC Middleweight champion ‘Marvelous’ Marvin Hagler, 62-2-2, in April of 1987 by split decision. 19 months later, he stopped WBC World Light Heavyweight champion Donny ‘Golden Boy’ Lalonde, 31-2.

In June of 1989, in a return match with Hearns, it ended in a split decision draw. In February of 1991, he lost to WBC Super Welterweight champion ‘Terrible’ Terry Norris, 26-3. Some 3 ½ years later in his final bout, he lost to IBC Middleweight champion Hector ‘Macho’ Camacho, 62-3-1, in 5 rounds. His final record was 36-3-1 with 25 stoppages.

Mayweather, Jr. won the WBC Super Featherweight title in October of 1998 stopping Genaro Hernandez, 38-1-1, in 8 rounds. In April of 2002 he won the WBC World Lightweight title in a disputed decision over Jose Luis Castillo, 45-4-1, then won the rematch.

He added the Light Middleweight title defeating Oscar ‘Golden Boy’ De La Hoya, 38-4, by split decision in May of 2007. His final record was 50-0 stopping MMA champion Conor McGregor, in 10 rounds, August of 2017.

Joe ‘The Brown Bomber’ Louis, 66-3 with 52 stoppages and 25 title defenses and 1960 Olympic Gold Medalist Muhammad ‘The Greatest’ Ali, 56-5 with 37 stoppages was a 3-time champion.

You pick the winners.

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Last Updated on 04/07/2025

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2025-04-08 03:03:29

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