11 Legendary Boxing Matches That Never Made it to the Ring

•

March 28, 2025 at 10:52 AM

Throughout boxing history, numerous potential mega-fights never materialized, leaving fans to wonder "what if?" Here are the most significant matchups that never happened:

Mike Tyson vs George Foreman Two heavyweight legends nearly met in the early 1990s and again in 1995 after Foreman's historic title win. Tyson's prison sentence and subsequent career trajectory prevented this explosive matchup.

Two men in business attire

Sugar Ray Leonard vs Aaron Pryor This fight was set for 1982 until Leonard's detached retina forced retirement. Pryor never got his shot at the welterweight superstar despite financial terms being agreed upon.

White boxer dog in t-shirt

Roberto Duran vs Alexis Arguello A potential lightweight clash in the late 1970s between these two legends never materialized as Duran moved up in weight.

Two men embracing in Panama

Jack Dempsey vs Harry Greb Despite reported sparring sessions where Greb dominated, this 1920s superfight never happened despite both fighters' interest.

Bill Paxton wearing dark suit

Floyd Mayweather Jr. vs Paul Williams The towering southpaw Williams presented a stylistic challenge that Mayweather never faced before his retirement in 2012.

Muhammad Ali with championship belt

Lennox Lewis vs Riddick Bowe Despite their 1988 Olympic bout, the professional rematch never happened despite both holding heavyweight titles in the 1990s.

Boxer helping fallen opponent upright

Juan Manuel Marquez vs Erik Morales These Mexican legends never met despite fighting in the same divisions for over a decade.

Boxer celebrates victory with raised arms

James Toney vs Chris Eubank Sr. Despite Toney's public challenge in 1993, this super-middleweight clash never materialized.

Shirtless boxer wearing mouthguard

Sugar Ray Robinson vs Charley Burley Robinson's manager later admitted to avoiding the dangerous Burley during their era.

Sugar Ray Robinson in boxing stance

Miguel Cotto vs Ricky Hatton This potential classic between 2006-2009 never came to fruition despite both fighters competing in the same weight classes.