25 Years Ago Tuesday Evander Holyfield Stunned Mike Tyson

It’s one of the most memorable Heavyweight title fights of the last 50 years, as Evander Holyfield made Heavyweight Championship history 25 years ago tonight with his upset “Iron” Mike Tyson.

The highly-anticipated battle took place on November 9th 1996 in Las Vegas and was for Tyson’s WBA World Heavyweight Championship.

It was a fight more than five years in the making after Tyson had been stunned by Buster Douglas for the first loss of his career and had the Undisputed Championship taken off of him in Tokyo, Japan, in February of 1990.

As we wrote previously, Holyfield took the Undisputed Crown away from Douglas with a single booming right hand in a third-round knockout eight months later in October of that year.

However, Holyfield held that championship only two years before Riddick Bowe upset him by 12 round split decision in November of 1992. In the meantime, Tyson had been convicted of rape in 1992 in Indiana and served three years in prison before being released in the spring of 1995.

While Tyson was “away,” Holyfield had regained part of the title by beating Bowe in 1993, but Michael Moorer upset Holyfield by decision to take his titles in 1994. Holyfield was also mis-diagnosed with a heart condition that forced him to retire for a brief time before he returned to fight a contender fight or two and wait for a title shot.

Tyson returned to the ring in 1995 with a couple of wins and beat Frank Bruno for the WBC version of the Heavyweight title. However, he was stripped of that belt for refusing to fight number one contender, Lennox Lewis and instead opting to fight WBA lesser-known champ, Bruce Seldon.

Tyson won easily over Seldon in a highly questionable first round knockout, where it did not look like Selden got hit with a clean punch, yet stayed down and was counted out. That led to the match up with Holyfield billed simply as “Finally” on a thrilling night at the MGM Grand Garden Arena on the Vegas strip.

On that night, it was more of the same for Tyson as his Douglas upset loss. This, as Holyfield stood up to Tyson, hit him hard and did not back down as the fight wore on.

One controversy emerged, as Tyson repeatedly lunged in with his head and Holyfield would lower his to duck and they would clash. Eventually, Mike was cut over the left eye in the sixth round from one of those. Referee Mitch Halpern deemed it to have been accidental head clash and the fight continued.

Holyfield scored a questionable knockdown in that same round, when he caught an off-balance Tyson with a punch to the chest. And, Tyson seemed to trip more than being knocked to the canvas. Nevertheless, it was ruled a knockdown.

Later in the seventh round, Tyson again leaped in at Holyfield for another head clash rom which Tyson cried out and winced from with his knees buckling. The referee took him over to the ring doctor, who briefly checked Tyson and allowed the fight to continue.

As the next couple of rounds wore on, Holyfield continued to land hard combinations and in particular left hooks. And, Tyson was once again reduced to simply being a one punch fighter in response, while getting tired.

Finally, in the 10th round Holyfield staggered Tyson with a good right hand and Holyfield chased him along the ropes landing two or three more significant punches just before the bell. A weary and bleeding Tyson was clearly in big trouble, but was still allowed to come out for the 11th round.

Almost immediately Holyfield jumped all over Tyson again and staggered him along the ropes with a combination of punches. With two lefts and a right landing on Tyson, it was enough for Halpern to jump between them and give Holyfield a shocking upset TKO win.

Holyfield improved to 33 – 3 with the KO win that night and joined Muhammad Ali at that time as the only fighter to ever regain at least a portion of the heavyweight championship on two occasions.

The humbling loss for Tyson was only the second of his career dropping him to 45 – 2, but he would never regain even a portion of the championship.

This was especially after their bizarre chaotic “Bite Night” second fight where Tyson was disqualified in the third round of the June 1997. That’s because Tyson had bitten off a portion of Holyfield ear causing the fight to be stopped and Holyfield to be declared the winner.

In, the present day of 2021, there had been rumors that Tyson and Holyfield would fight at least an exhibition for a third bout, while both of them are in their 50s. However, that never happened in 2020, as Tyson returned to the ring and fought Roy Jones Jr. instead.

Holyfield later tried to return at 58 years of age in September of 2021 and looked horribly slow and overmatched in a one-round exhibition loss to former UFC light heavyweight champion, Vitor Belfort.

Still, Holyfield is a Hall of Famer, who beat Mike Tyson while they were both in their primes 25 years ago.