Before Anthony Joshua vs Tyson Fury’s decade-long wait, Mike Tyson and Evander Holyfield took 12 years to finally fight

The wait for Tyson Fury and Anthony Joshua has become one of boxing’s longest-running heavyweight stories. The British rivals have talked about fighting for years, but the much-anticipated clash has repeatedly remained out of reach.But heavyweight boxing has seen even longer waits. Mike Tyson and Evander Holyfield first appeared destined to meet in the late 1980s. Contracts were signed, plans were made, and then everything fell apart. It took years before they finally shared a ring, creating one of boxing’s most famous rivalries.Mike Tyson and Evander Holyfield showed how long a heavyweight fight can takeThe Mike Tyson-Evander Holyfield story began long before their professional rivalry. The two heavyweights had crossed paths at the 1984 American Olympic boxing trials. A pool-table incident added another layer to their relationship, and their careers continued moving toward an inevitable showdown.By October 1989, that fight appeared to be finally happening. Contracts for Tyson and Holyfield had reportedly been signed for a summer 1990 meeting.The planned fight was scheduled for June 18, 1990, in Atlantic City. Then came one of boxing’s biggest shocks. On February 11, 1990, Tyson lost his heavyweight titles to Buster Douglas in Tokyo.A new agreement was eventually reached on July 11, 1991, at a New York hotel. The fight was set for November 8, 1991, at Caesars Palace in Las Vegas.The financial numbers showed just how important the fight had become. The fighters were expected to split a $45 million guarantee, with Holyfield receiving $30 million. The event was projected to generate around $100 million.Once again, however, the fight collapsed.Tyson was arrested in July 1991 after travelling to Indiana for a beauty pageant. He was charged with rape. The proposed fight was pushed back, with January 1992 discussed as a possible new date. Then Tyson suffered a rib injury. The fight was off again.Tyson was later convicted and sent to prison. For several years, a Tyson-Holyfield fight looked impossible.But boxing rarely closes the door completely on a major money fight.After Tyson was released from prison in 1995, discussions about Holyfield resumed. The matchup still had enormous commercial value.Tyson regained the heavyweight championship in 1996. Holyfield, meanwhile, had experienced his own difficult road. He had lost the title, regained it and then lost it again.Finally, the fight was officially announced for November 1996 at the MGM Grand in Las Vegas.Many expected Tyson to win. Instead, Holyfield delivered one of the biggest upsets of his career. He stopped Tyson in the 11th round.The rematch in 1997 became even more infamous. Tyson was disqualified after biting Holyfield’s ears in what became known as the “Bite of the Century.”That history provides an interesting backdrop to Fury and Joshua. Joshua first called for the fight in April 2016, after winning a heavyweight world title. More than a decade has now passed since the rivalry first became a serious talking point.The circumstances are different, but the pattern is familiar. Negotiations, changing champions, promoters, money and timing have repeatedly stood between two of the biggest names in British boxing.Stay updated with the latest Asian Games 2026 news, check the Asian Games medal tally and complete Asian Games schedule.Get the latest Sports News and Live updates. Download the TOI app.