The Greatest Sports Upset Ever Took Place 26 Years Ago Today, Here’s How It Happened

No matter if you’re a 31-year-old like myself, a gray-haired who revels in the old days or a college kid still living in a dorm, there’s no doubt that you know about the greatest sports upset ever: the Mike Tyson-Buster Douglas bout.

Occurring 26 years ago today, February 11, 1990, when Douglas sent Iron Mike to the canvas during their bout in Tokyo, it changed the sports landscape forever, giving one boxer the moment of his lifetime and sending the other into a free fall.

Not only was Douglas battling, arguably, the most feared man in sports at that time, who carried a 37-0 career record into the ring that night, but he was up against 42-1 odds, leaving many to wonder if he’d even make it out alive.

He did more than just survive, he conquered—and this is how it happened.

For Tyson, this was the first time in which he finally let down his guard and believed he was untouchable, even admitting as much years later about his pre-fight mindset, per

“On January 8, 1990, I got aboard a plane to fly to Tokyo. Kicking and screaming. I didn’t want to fight; all I was interested in then was partying and women.”

Even during training prior to the bout, Tyson seem disinterested and uninspired, as sparring partner Greg Page gave the heavyweight champ such a beating that legendary boxing promoter Don King grew concerned.

As for Douglas, he had nothing to lose going in against Tyson.

Carrying an unimpressive 29-4-1 career record into the fight, Douglas was hungry for the opportunity to snatch the WBC, WBA and IBF title belts from Tyson, using motivation from personal struggle to inspire himself to become the next heavyweight champ.


This was a 29-year-old Douglas who was motivated and focused because of three serious personal struggles he was facing. First, Douglas was heartbroken over the death of his mother, who passed away less than a month before the fight. Also, the mother of Douglas’ then-11-year-old son, Lamar, was seriously ill. Douglas had also recently separated from his wife.

It’s with that motivation that Douglas maintained laser focus, not taking for granted the opportunity that presented itself.

The night before the fight, things didn’t change for Tyson, as he later admitted he was partying into the early hours, and never even studied film of Douglas’ fighting tactics.


“The day before the fight I had two maids at the same time,” Tyson recalled. “And then two more girls, one at a time, the night before the fight.”

The fatigue from Tyson showed throughout the fight, as Round 1 turned into Round 2, and then 3… 4… 5… 6… 7… but, finally, in the eighth round, Tyson sent Douglas to the mat, leaving the challenger woozy and trying to maintain his balance in getting to his feet.

If not for a communication problem between Mexican ref Octavio Meyran and the Japanese timekeeper, Douglas may have been ruled down, as Meyran was accused of a long count—nearly 12 seconds, according to Don King.


After the fight, Meyran’s count would become the focal point of a major controversy. Tyson and King asserted that his count was too long — at least 12 seconds — and that Tyson should have been declared the winner. To this day, King still blames Meyran for a supposed long count he believes cost Tyson the fight.

While the controversy ensued, it became a moot point by the end of the fight, as the bout wavered on and, finally, in the 10th round, it happened, as commentator Jim Lampley aptly called out:

“What an uppercut by Douglas! And down goes Tyson.”

At that moment, the boxing world, sports world and both fighters’ lives would never be the same, as Tyson fell into a dark hole that, eventually, led him to prison for his violent temper and internal demons, as Douglas became a one-hot wonder, losing his IBF title belt to Evander Holyfield in his next fight.

Said King, per ESPN:

“Nobody could beat Tyson but himself, and he beat himself… He fell short there because he began to believe his own headlines. He took this guy lightly.”

“I didn’t think Buster would beat Tyson. If I said that I’d be telling a lie. But did he have a chance because he got the opportunity? In boxing, yesterday’s nobody can become tomorrow’s somebody. The man who wants it the most is going to come home with it. He had the will to win.”

And with that, just when no one believed it could happen, David did slay Goliath, and it’s the most shocking upset sports has ever seen.


Nick Dimengo avatar
Nick's a Sr. Editor for BroBible, mainly relying on his Sports Encyclopedia-like mind to write about things. He's also the co-host of the BroBible podcast "We Run This," and can be seen sweating his ass off while frequently running 10+ miles around Seattle.