Boxing’s Biggest Upsets

November 15, 2023
6 months

Boxing has a rich history of surprising moments and underdog victories. Throughout the years,
numerous fighters have defied the odds. In this article, we will explore some of the most
significant upsets in boxing history.

Buster Douglas vs Mike Tyson


Buster Douglas’ victory over Mike Tyson is considered the gold standard for upsets. Heading into their title bout, Tyson sported a 37-0 professional record, with most of his wins coming via knockout. Douglas, on the other hand, had blown his first chance to secure a title when he faced Tony Tucker for the IBF heavyweight title.

On this day in 1990, the shock of all shocks as Buster Douglas stopped Mike Tyson in Tokyo

— DAZN Boxing (@DAZNBoxing) February 11, 2023

In a stunning turn of events, however, Douglas held his own as the fight progressed, surviving the count when Tyson dropped him in the eighth round. He went on to knock Tyson out in the tenth round.


Leon Spinks vs Muhammad Ali


In 1978, a young Leon Spinks with only seven professional fights under his belt took on the legendary Muhammad Ali, who was nearing the end of his career. Many believed that Spinks lacked the experience to defeat Ali, but he had other plans.


Spinks put on the best performance of his boxing career, edging out a split decision victory over Ali. Unfortunately for Spinks, he lost the rematch.

Leon Spinks upset Muhammad Ali OTD in 1978 to win the heavyweight world title in Las Vegas. Here’s most of the 15th round, one of the great final rounds in the history of heavyweight title fights. VC: glashek

— Ringside Seat (@RingsideSeatMag) February 15, 2023

Randy Turpin vs Sugar Ray Robinson


In 1951, Randy Turpin faced off against Sugar Ray Robinson, who was on a 90-fight winning streak. However, Turpin proved to be a better fighter, taking full advantage as Robinson began to tire later in the fight.

This earned him a decision victory. Robinson got his revenge and knocked Turpin out in the rematch.

Muhammad Ali vs Sonny Liston


Sonny Liston was coming off consecutive wins against Floyd Patterson. Many people expected things to go bad for the big-talking Ali.

Ali shocked the world by outclassing Liston so severely that he quit on his stool after only six rounds. This fight marked the beginning of Ali’s legendary career and showcased his ability to back up his words.

James Braddock vs Max Baer


This colossal upset led James Braddock to become known as “The Cinderella Man,” and his story became an award-winning movie. Max Baer was a powerful puncher with a reputation for knocking opponents out.

And yet, Braddock surprised fans with his ability to take a shot, took everything Baer had, and kept walking forward.

This earned him a unanimous decision win. Unfortunately for Braddock, his title reign was short-lived as he lost his next fight to Joe Louis.

Max Schmeling vs Joe Louis


Joe Louis had already established himself as a force to be reckoned with in the heavyweight division when he squared off against Schmeling. Sporting a 24-0 professional record, few expected Schmeling to put up much of a fight.


However, Schmeling had appropriately prepared. His hard counter rights kept finding their target, and he eventually put Louis away with his barrages during the twelfth round, handing the ‘Brown Bomber’ his first loss. Louis went on to knock Schmeling out in the rematch.

Evander Holyfield vs Mike Tyson


Holyfield was considered a washed-up boxer then, and he opened up as a 25:1 underdog. However, Holyfield lived up to his nickname “The Real Deal” and showcased it to the boxing world. Holyfield frustrated Tyson by outboxing him.

He knocked him out in the 11th round and proved his victory wasn’t a fluke by dominating their rematch before Tyson was disqualified for biting his ear.


Muhammad Ali vs George Foreman


This was one of the biggest fights that ever took place in boxing history, and it lived up to the hype. Foreman was the reigning WBC, WBA, and Ring heavyweight champion.

Ali was also established at that point, but Joe Louis and Ken Norton had beaten him. Many didn’t give Ali much of a chance, but that didn’t stop him from throwing every insult he could at Foreman.

Ali backed his talk up inside the ring, using the rope-a-dope strategy to tire Foreman before knocking him out in the eighth round.


Boxing has given the world some of the most shocking upsets and underdog victories throughout its history. And we can look forward to more stunning upsets in the future.