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Buster Douglas Over Mike Tyson Remains Boxing's Greatest Upset cover image
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TJ Rives
Feb 10, 2026
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February 10th, 1990 in Tokyo, Mike Tyson was seemingly indestructible. However, James "Buster Douglas" changed that in under an hour with the performance of a lifetime, as he knocked Tyson flat to become undisputed heavyweight champ.

36 years ago in Tokyo, Japan, James “Buster” Douglas delivered what is still widely regarded as the greatest upset in boxing history and potentially, one of the single greatest upsets by any athlete or team ever recorded.

That February 10th night (in the U.S.) in the Tokyo Dome, Douglas didn’t simply defeat Mike Tyson by knockout — he shattered the aura of invincibility surrounding the undefeated, undisputed heavyweight champion.

And, it forever altered the sport.

Entering the fight that winter night four decades ago, Tyson was seen as unbeatable.

He had demolished challenger after challenger with frightening speed and power to amass a 37-0 record, and no opponent in his professional career had truly stood up to him.

Douglas, who was 28-4-1, when he headed to the ring that night,  was viewed as little more than a sacrificial challenger. Las Vegas oddsmaker Jimmy Vaccaro was the only one to get any action in the weeks leading up to the bout. And after, a couple of massive bets came in on Tyson to win very little money, he listed him as a staggering 42–1 underdog. And, very few believed the fight would last long.

From the opening bell, however, it was clear something was different. Douglas controlled the fight with his size, longer reach, and an authoritative left jab that repeatedly snapped Tyson’s head back. He followed it with sharp straight right hands and right hooks, consistently beating Tyson to the punch and winning round after round. Never before had Tyson been outboxed so thoroughly or so confidently.

Douglas’ performance was particularly remarkable given his history. He had often shown flashes of brilliance but failed to deliver in career-defining moments. Most notably, in his 1987 IBF world title fight against Tony Tucker, Douglas built an early lead only to fade badly, eventually being stopped in the 10th round. That reputation for falling short lingered — until Tokyo.

Motivation played a powerful role. Just weeks before the fight, Douglas’ mother had passed away suddenly. Fighting in her memory, he arrived in Tokyo in the best shape of his life, determined to seize the moment. On that February Sunday afternoon — live late Saturday night in the United States — Douglas rose to the occasion in spectacular fashion.

Even with his left eye nearly swollen shut, Tyson remained dangerous, capable of ending the fight with a single punch. And that led to the fight’s most dramatic moment to that point in the eighth round. That's when Tyson finally broke through with an uppercut and knocked Douglas down. Douglas rose, while referee Octavio Meyran counted and reached nine.

It was a moment many expected to signal the end. But, Douglas showed tremendous resolve, as the round ended when he rose and he immediately control in the ninth, staggering Tyson along the ropes by his own corner with a several huge punches.

In the 10th round, Douglas delivered the "all time" finish in boxing history. He landed a massive right uppercut of his own that staggered Tyson, followed by a crushing left hook to the jaw that sent the champion's mouthpiece flying and his body crashing to the canvas — the first knockdown of Tyson’s professional career.

Tyson struggled to rise, fumbling with the mouthpiece and inserting it backwards as Meyran thundered the count of 7, 8...9!  When Tyson reached his feet, Meyran looked into his eyes and waved the fight off, declaring a technical knockout.

HBO hall of famed broadcaster Jim Lampley captured the moment perfectly at ringside, proclaiming, “Let’s go ahead and call it the biggest upset in the history of the sport… James ‘Buster’ Douglas, Undisputed Heavyweight Champion of the world.”

36 years on, the images still remain unforgettable:

Tyson buckling from the uppercut, standing defenseless under Douglas’ assault, and struggling to all fours with the thousands in Tokyo and millions watching on TV in  disbelief.

Re-live the Douglas monumental KO here:

Douglas' title was gone as quickly as he had won it, when Evander Holyfield kayoed him with one punch in October later that year.

Tyson went to prison for a rape conviction in Indiana in February of 1992, spending three years there.

He and Douglas never met, again.

Still, no upset, before or since, in the history of championship boxing has matched the shock, significance, and lasting impact of James "Buster" Douglas stunning Mike Tyson in February 1990.