Everyone wanted him to fight Holyfield, who was undefeated but was bumping up from cruiserweight to heavyweight. Holyfield would be in attendance for Tyson’s next fight against Buster Douglas at the Tokyo Dome in 1990. Many believed a fight between the pair would be announced following what many thought would be another knockout for Tyson.

Tyson’s corner was so confident he would win that they didn’t bring an enswell. Late in the fight, Douglas had peppered Tyson so much that they couldn’t control the swelling. Online boxing news shows that Douglas would shock the world by knocking Tyson out in the 10th round.

The first planned fight with Holyfield didn’t materialize, as he would fight Douglas instead.

Prison Sentence Keeps Tyson Out for Four Years

Following the loss to Douglas, Tyson would pick up four more wins before he faced controversy outside of the ring. In July 1991, Tyson was arrested for raping a woman in an Indianapolis hotel room. Tyson claimed the events were consensual, but the jury found him guilty.

He would end up serving several years in jail before he returned to the ring in August 1995. Tyson would win his return fight in August 1995 by disqualification. He ended up picking up the WBC and WBA heavyweight titles by beating Frank Bruno and Bruce Seldon. 

The four-fight winning streak was enough to get him a chance to fight Holyfield according to heavyweight boxing news.

Holyfield Fights Series of Tough Heavyweight Bouts as Champion

Holyfield is the only fighter in boxing history to be the undisputed champion at both cruiserweight and heavyweight. Following Tyson’s stunning defeat to Douglas, Holyfield made his run as undisputed champion short. Holyfield stopped Douglas in three rounds.

Holyfield would go on to defend his titles four times before losing to Riddick Bowe in November 1992. While Holyfield won his rematch with Bowe a year later, he only recaptured the WBA and IBF heavyweight titles. Heading into the first meeting with Tyson, Holyfield had lost two of his previous four fights and wasn’t holding any championships.

Wrong Fighter Favored?

While many looked at Holyfield as past his prime for his first fight against Tyson, making him a 5-to-1 underdog, there hadn’t been much to be excited about for Tyson since his return. His best win before fighting Holyfield was a win over Frank Bruno, whom Tyson had already knocked out before he went to prison.

Holyfield put on a boxing clinic against Tyson. He answered Tyson’s hard single shots with extended and accurate combinations. In the sixth round, Tyson did get cut from a headbutt from Holyfield, but the clash of heads was ruled to be incidental. Holyfield leaned on his superior strength and technique, eventually forcing a stoppage in the 11th round.

Rematch Disgraces the Sport

The second fight between Holyfield and Tyson is the one everyone remembers. It’s hard to blame anyone for that. It’s not every day that someone has to be told to stop boxing because he refuses to quit biting his opponent.

But that’s what Tyson did. Tyson claims he bit Holyfield because of a headbutt in the second round. He was also upset about the clashes of heads during the first bout. But the second fight between Tyson and Holyfield was stopped due to the chaos in the third round.

When Would Have Produced the Best Fight Between the Two Men?

Douglas’ story of winning as a sizable underdog is one of the best in American sports history. But it’s hard not to wonder what that fight between Tyson and Holyfield would have been like in 1990. But Tyson not training seriously for Douglas shows he was already starting to let his intensity for the sport slip away.

Not beating Holyfield, Riddick Bowe, or Lennox Lewis leaves Tyson on the outside of truly claiming he was the greatest heavyweight ever. He never fought Bowe but lost to the other two. The best time for Tyson and Holyfield to have fought would have likely been 1987 or 1988.

Tyson’s mentor and trainer, Cus D’Amato, died in 1985. Many people point to that as the time when a lot of negative outside influences started to impact Tyson. But the fallout from that didn’t start to show up until around the time of the Douglas fight.

In his prime, it would be entertaining to see how Tyson handled Holyfield and if a more disciplined version of him could have given him an important resume win, according to boxing updates tonight.

By Dean McHugh