Activities Sports & Athletics Roy Jones vs Mike Tyson Who Would Have Won? Share PINTEREST Email Print beforeitsnews.com Sports & Athletics Boxing Baseball Basketball Bicycling Billiards Bodybuilding Bowling Car Racing Cheerleading Cricket Extreme Sports Football Golf Gymnastics Ice Hockey Martial Arts Professional Wrestling Skateboarding Skating Paintball Soccer Swimming & Diving Table Tennis Tennis Track & Field Volleyball Other Activities Learn More By Niall Doran Writer Niall Doran specializes in boxing and kickboxing. He created the site Boxing News and Views, and his writing has appeared in Boxing Scene and HuffPost UK. our editorial process Niall Doran Updated July 22, 2018 Although this is a fight that probably had a very short, two-year time frame of ever happening in the past, and it is one that really would have appealed to boxing fans for a variety of reasons. Roy Jones became one of only two men ever in the history of the sport to win titles at middleweight and incredibly at up at heavyweight when he claimed a version of the heavyweight title by defeating John Ruiz over the duration on points. At the time of the fight (both in the build-up and post-fight) a possible showdown between Jones and Tyson was certainly mentioned, but never quite came to fruition. The Possibilities of a Fight When Roy fought Ruiz his father (who played a key part in Jones' career early on) said that he would never endorse such a fight with a man like Tyson, where he felt Roy would be giving away a remarkable amount of physicality against a much bigger opponent stating "That's just too much mass". Granted, you can see the genuine concern and love of a father for a son there, but Jones at that time could very well have had too much speed, elusiveness and general ring craft for an aging Tyson around the 2003/2004 period (near the end of Tyson's career). Of course, the flip side of the argument is that people more than likely will argue about Jones' chin (which went on to prove fragile as he aged) would have made him short work for a guy like Tyson, even at the end of his career. Then again, that was when Jones won the heavyweight title and moved back down to light-heavyweight and one could also argue, that he should never have done that in the first place and that in doing so, was physically not in an aging athlete's best interest in terms of weight draining himself and dehydration. How It Would Have Gone Down The fight itself, notably, would have been in a time where both men were outside of their primes (Tyson more so than Jones) but due to the popularity, a fascinating clash of styles and explosive fighting reputations of both warriors, would have made for one hell of a show. Essentially you'd be pitting the dazzling speed and flashy combinations of Jones against the relentless, one-punch knockout power of Tyson. From a technical point of view, you'd think that if Tyson was to catch Jones at any point of the fight that Roy would have been out of there, but would Tyson at that late stage of his pro campaign (after been KO'd by Lennox Lewis) had enough guile and general motivation to get himself in the shape necessary to do so? It could have made for an intriguing show and payday for both guys late on into their careers but if you look at how it may have unfolded, Jones would have had a bit too much for "Iron Mike" at that late stage of the game. You could almost imagine Tyson coming out like a bull in the early rounds looking to catch Jones with that one shot while eating some fast jabs and combinations during an attempt to get inside. As the fight unfolded Jones' quick, stinging attack and evasive style would have probably broken Mike late down the stretch but would he have had enough pop to actually to stop Mike? Tyson would have been mercifully pulled out by his corner in a late Roy Jones TKO. Two of the most exciting fighters of their generation, what a spectacle it would have been.