They had both fought at the highest level, with Tyson winning the WBC title in 1986 and Holyfield winning the WBA title the same year.
However, they had never fought each other professionally, although they had reportedly sparred together as teenagers on the amateur circuit. One reason they had not met sooner was because Tyson always fought at heavyweight, whereas Holyfield was a cruiserweight in his 20s.
They became acquaintances while preparing for the 1984 Summer Olympic Games, although in different weight categories. During the preparations, Holyfield beat Ricky Womack to qualify for the US team, while Tyson failed to make the final cut, as he lost to Henry Tillman.
When they finally met in Las Vegas, Nevada, on 9th November 1996, Tyson, 30, was the younger of the two boxers, with Holyfield, 34, in the fourth match of his comeback, after retiring in 1994. The WBA heavyweight title match was momentous, as Tyson was the outright favourite to win, with Holyfield considered by some pundits to be washed up.
Seeing former youth prodigy “Iron Mike” Tyson finally meet the only four-times world heavyweight champion Holyfield was something the boxing world had wanted for a long time. Despite Holyfield being considered the underdog, it was still a match that caused a massive flurry of anticipation.
Brooklyn-born Tyson had come onto the pro boxing scene like a hurricane in the 1980s. His boxing abilities were discovered at school and he was introduced to coach Cus D’Amato. Tyson dropped out of high school to pursue boxing as a career and won gold medals at the Junior Olympic Games in 1981 and 1982 as an amateur.
At the age of 18, in his first professional fight, he beat Hector Mercedes on 6th March 1985, in Albany, New York. Winning his first 19 professional fights by knockout, he won the WBC title in 1986, at the age of 19, beating Trevor Berbick in the second round. In 1987, he added the IBF and WBA titles to his tally after defeating Tony Tucker and James Smith. He was the only heavyweight to unify all three titles in succession.
In 1988, Tyson knocked out Michael Spinks in the first round to become the lineal heavyweight champion. Known for his ferocious and intimidating boxing style, he dominated the heavyweight division in the 1980s and ’90s.
Born in Atmore, Alabama, in October 1962, Holyfield began boxing aged seven, winning the Boys’ Club boxing tournament and going on to compete in the Junior Olympics at 13. Like Tyson, he was a youth prodigy.
He became Southeastern Regional Champion at 15, also winning the Best Boxer Award. By the time he was 22, in 1984, he had already won 160 matches, 76 by knockout, and lost only 14. Holyfield won a bronze medal at the 1984 Olympics, as an amateur, in the light heavyweight class, before moving up to cruiserweight in July 1985. He won his first world championship in 1986, defeating Ricky Parkey and Carlos de León respectively to win the WBC and IBF titles, successfully defending his titles three times.
Holyfield announced his retirement from boxing in 1994 due to medical advice. However, he returned to the ring in 1995, after having been given a clean bill of health.
Tyson v Holyfield
The fight between Tyson and Holyfield, in Las Vegas in 1996, followed a string of victories for Tyson against boxers not quite at his level such as Buster Mathis Jnr, Peter McNeeley and Bruce Seldon. Meanwhile, Holyfield was still semi-retired, leading to Tyson being 17-1 favourite over his opponent.
Holyfield proved his doubters wrong, as the two heavyweights slugged their way through 11 rounds. He outclassed Tyson with his movement, although he also headbutted his opponent, allegedly accidentally – Tyson thought otherwise. Eventually, Holyfield won by a technical knockout and the fight didn’t see a 12th round.
It was a massive upset and Tyson was hugely disappointed. However, it paved the way for a rematch, with both fighters agreeing to meet a second time.
The rematch took place at the MGM Grand Garden Arena in Las Vegas on 28th June 1997. Both fighters did well financially, with Holyfield receiving a $35 million purse and Tyson getting $30 million.
The referee from the first match, Mitch Halpern, voluntarily stepped aside, after Tyson claimed he failed to act on Holyfield’s headbutts first time round. He was replaced by referee Mills Lane. The crowd was full of A-list celebrities, while almost two million households bought the event on pay-per-view TV.
The match got off to an exciting start, with Holyfield winning the first round, although Tyson came out blazing for round two. Holyfield appeared to headbutt him again, opening up a cut over Tyson’s right eye. As the fight went on, it started to impair his vision, which frustrated Tyson further. During round three, with 40 seconds left on the clock, Tyson’s aggression appeared to be overpowering Holyfield, but what followed shocked not only the boxing world, but also the fans.
As the fight continued, wearing his mouthpiece, Tyson bit Holyfield’s right ear, causing the latter to jump in pain and shock. The referee seemed unaware of what had happened at first, but Holyfield’s trainers enlightened him.
Lane intended to end the fight, but as Holyfield seemed uninjured, apart from a bloodied ear, he allowed it to continue. Unbelievably, Tyson bit Holyfield’s left ear before the end of the round. This time, Lane disqualified Tyson outright before the fourth round had begun, awarding the title to Holyfield.
After the fight, Tyson admitted what he had done, but wasn’t in the mood to apologise. He said he had lost control, due to his frustration at Holyfield headbutting him again. He described the incident as Holyfield getting a “nick on his ear”. Tyson felt his response was justified, claiming, “This guy keeps butting me,” and adding, “I’ve got to retaliate.”
However, two days later, Tyson finally apologised, but he lost his boxing license in the state of Nevada and was fined $3 million – the largest fine in the sporting world at the time. He never fully shook off the stigma of the biting incident.
Five years later, when Tyson was due to fight Lennox Lewis in 2002, Nevada refused to restore Tyson’s boxing license, so the match took place in Memphis, Tennessee. Lewis defeated Tyson by knockout in the eighth round.
Tyson continued boxing until his retirement in 2005, while Holyfield retired in 2011. The two fighters met again over the years on TV interviews, even discussing what had happened. Reports suggest they have become friends.
Tyson returned to the ring briefly for an exhibition match against Roy Jones Jnr, which was declared a draw, in 2020.
Media reports surfaced that Tyson, 54, and Holyfield, 58, were planning their third fight, with a purse of £200 million. On 7th February, Tyson’s friend, Zab Judah, claimed the fight would take place in Dubai, suggesting the rematch had already been agreed.
In January, Holyfield had said his team was in talks with Tyson’s camp. Now, Judah says the deal is “signed, sealed and delivered”. Boxing fans are eagerly awaiting further updates to see if the third meeting between the two boxing greats is as explosive as their previous two.