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The Grueling Truth - Where Legends Speak / The Grueling Truth's Top 10 Sports Lists / Top 10 Heavyweight Boxing Upsets of All Time: Which Upset was the Most Shocking?

Top 10 Heavyweight Boxing Upsets of All Time: Which Upset was the Most Shocking?

Publish Date: 04/29/2024
Fact checked by: Mark Lewis

What’s more exciting than the heavyweight Champion of the World getting upset? Heck, Sylvester Stallone became a Billionaire off the concept! Today we are going to countdown the top ten nights when the title changed hands, surprisingly.


Let’s face it: some of these upsets, in hindsight, are not as big as they were at the time they happened. Muhammad Ali is on this list twice, but in hindsight, they really were not that great of upsets; we just didn’t understand how special a fighter he was at that moment in time. So the criteria has a ton to do with the odds going into the fight and the publics perception that the fight was a mismatch.

10) Hasim Rahman defeated Lennox Lewis

Lewis was coming off an impressive performance against David Tua and appeared at his peak. Rahman was considered an outstanding fighter but widely perceived as vulnerable to knockout. Lewis entered at his highest weight so far and got knocked out with a tremendous right hand near the end of round five.

This fight was fought in the early morning hours in Africa and was not considered dangerous for Lewis. After Lewis had already been upset by McCall, you would think that Lewis would have taken this fight more seriously than he did. Lewis did take the rematch seriously and easily knocked out Rahman in the rematch.

Video: Lennox Lewis vs Hasim Rahman I - Highlights (Upset & KNOCKOUT of the Year)

Lennox Lewis vs Hasim Rahman I – Highlights (Upset & KNOCKOUT of the Year)

9) Evander Holyfield KO 11 Mike Tyson

People tend to forget that Tyson was on a roll going into this fight, while Holyfield looked old in three out of his last four fights while winning only two of them. Tyson started as the 25-1 favorite before becoming 10-1 by fight time; ultimately, Holyfield proved stronger physically and psychologically than Tyson. This fight is considered one of the Greatest Heavyweight Fights of all time.

Holyfield was the stronger fighter, using his strength to bully Tyson around the ring. During the fight, Tyson was flat-footed and unprepared for this, and Holyfield beat Tyson easily. The fight was dirty as both fighters used their heads and clinched a lot. No doubt existed after this fight which man was better.

Video: Mike Tyson vs Evander Holyfield 1 //

Mike Tyson vs Evander Holyfield 1 // “Finally” (Highlights)

8) Max Schmeling stops Joe Louis

Max was considered an over-the-hill fighter going into this matchup with the seemingly unbeatable Brown Bomber. Schmeling, who had knocked out former Champions Primo Carnera and Max Baer earlier in his career, had held the title for a while a few years earlier. Schmeling may have been considered old and over the hill; nevertheless, he saw Louis’ weakness immediately and knocked him out in stunning fashion.

Times as they were back then meant Louis still got the shot at Braddock’s title because of fear that a Schmeling/Braddock matchup would have led to Hitler keeping Schmeling from defending his title against Louis. Yes Joe Louis was upset, but it was at a young age and never happened again.

Video: Joe Louis vs Max Schmeling 1 // Highlights

Joe Louis vs Max Schmeling 1 // Highlights

7) Oliver McCall defeated Lennox Lewis.

McCall was an inconsistent heavyweight who experienced both wins and losses. Lewis appeared unbeatable going into this bout; being young, strong and fast were his hallmark characteristics; however, McCall managed to land an unbelievable right hand that stopped Lewis within two rounds and ended his unbeaten streak.

Lewis had two times during his career that ended up on this list, and in the end, I think that is what separates him from the Ali, Marciano and Louis of the boxing world. I can see it happening once, but not twice. Lewis is still an all-time great Heavyweight, but being on this list does tarnish it a bit.

Video: WHEN CHAMPION GOT DESTROYED | Lennox Lewis vs Oliver McCall 1

WHEN CHAMPION GOT DESTROYED | Lennox Lewis vs Oliver McCall 1

6) Michael Spinks UD 15 Larry Holmes

No Light Heavyweight Champion had ever defeated a Heavyweight Champion before Spinks out-hustled Holmes to win a close decision! In just three months, Spinks gained over twenty pounds thanks to nutritionist Mackie Shilstone. Whatever he did at training tables or during workouts paid dividends as Spinks beat Holmes consistently and eventually secured an excellent decision win against him.

Michael Spinks would win the rematch, but many thought Holmes did enough to win that fight. In the end, Spinks beats an ageing, bored Champion in an entertaining fight. Spinks used constant angles and peppered the slowing champions constantly during the fight.

Video: Larry Holmes vs Michael Spinks l (Highlights)

Larry Holmes vs Michael Spinks l (Highlights)

5) Leon Spinks SD 15 Muhammad Ali

Spinks was only in his eighth professional fight and, just two fights earlier, had struggled to a draw with Scott LeDoux in a bout many believed LeDoux won. On the other hand, Ali was slower but still had enough strength to defeat Earnie Shavers just months earlier. Ali tried the rope a dope against Spinks, but Spinks proved too strong and continued coming after Ali. As Ali would later state after their encounter, Spinks was relentless in attack.

Spinks was a relentless but under-sized Heavyweight, and what happened on that February night is easily explainable as Ali took the novice Spinks lightly, and he paid dearly for it. Ali would dominate the rematch in September and then retire. The rematch is considered one of the Greatest Heavyweight rematches of all time!

Video: Muhammad Ali vs Leon Spinks 1 // The Ring Magazine Upset of the Year (Highlights)

Muhammad Ali vs Leon Spinks 1 // The Ring Magazine Upset of the Year (Highlights)

4) Cassius Clay KO7 Sonny Liston

In this fight, the young Cassius Clay came face-to-face with what many considered an invincible opponent and demonstrated that no one is truly unbeatable. Clay may have won this fight mentally before it started, as he behaved like an emotional wreck in preparation. In reality, however, during the fight itself, he showed speed that few heavyweights have ever displayed — not even today.

The truth, looking back, is that Clay was way too skilled for Liston, and Liston had never faced anyone even close to Clay’s skill set. That is not Sonny’s fault because no heavyweight has ever lived with Clay’s skill set.

Video: Cassius Clay (Muhammad Ali) vs. Sonny Liston 1 - 1964 Full Fight in Color HD

Cassius Clay (Muhammad Ali) vs. Sonny Liston 1 – 1964 Full Fight in Color HD

3) James Braddock and Max Baer

This match-up occurred at Madison Square Garden Bowl, commonly called “The Graveyard of Champions,” because no reigning champion had ever successfully defended their titles there. Much to everyone’s shock and surprise, Baer seemed disinterested in fighting that night, and Braddock took full advantage by winning a close but just decision.

The fight was a relatively dull and listless affair that saw Braddock do just enough to lift the title from Baer. Of course, the movie Cinderella Man was based off this fight and the incredible story of Braddock winning it all.

Video: James Braddock vs Max Baer - Highlights (CINDERELLA MAN)

James Braddock vs Max Baer – Highlights (CINDERELLA MAN)

2) Muhammad Ali KO8 George Foreman

Ali was 32 and at what many believed would be the end of his career or so many thought. Foreman seemed invincible after knocking out Joe Frazier in two rounds. Many predicted Ali would meet a similar fate against Foreman; instead, he employed rope-a-dope tactics to tire him out and eventually knocked him out in eight rounds during an incredible and unforgettable battle.

Ali’s ability to take a punch made this win possible. Foreman had looked invincible up until this night in his career. Mentally Foreman was not the same the next three years and he would eventually lose to Jimmy Young in Puerto Rico and then retire. He came back a decade later and would miracuosly reclaim his title.

Video: Ali's Impossible Victory Explained

Ali’s Impossible Victory Explained

1) James Douglas knocked out Mike Tyson.

This fight was truly iconic! Mike Tyson had been dominating everything that came his way and was an overwhelming 42-1 favorite against “Buster”, while most had doubted Douglas’ heart after quitting against Tony Tucker. Most questioned how many fights were left in Douglas. On one February night in Tokyo, Japan, Buster Douglas proved special. Eventually, he left Tyson lying defeated on the canvas, searching for his mouthpiece!

Of course, Buster ruined the moment by eating himself up to almost 250 pounds and losing the title to Evander Holyfield, maybe that makes this upset even bigger? For that one night, though, Buster Douglas will be remembered forever.

Video: Mike Tyson vs. Buster Douglas

Mike Tyson vs. Buster Douglas

Honorable mentions

James J. Corbett defeated John L. Sullivan

Sullivan was 38-0-1 at the time, and considered himself an exceptional badass. Sullivan offered Corbett a purse of $25,000 plus an additional $10,000 side bet winner-take-all bet; Corbett took him up on it, boxing beautifully while slowly wearing down Sullivan until round 21 when Corbett floored him to become the second gloved Heavyweight Champion ever in history.

Gene Tunney UD Jack Dempsey I.

Dempsey and Babe Ruth were two of the most beloved athletes of the roaring 20s, and Dempsey took his popularity very seriously, fighting rarely as a result. Unfortunately, this caught up with him when Tunney took an easy win against Dempsey before over 120,000 spectators at Madison Square Garden. Tunney controlled this fight with ease and stunned Dempsey in front of everyone!

Andy Ruiz Jr defeated Anthony Joshua

Ruiz had been an excellent pro heading into this fight, while most fight fans thought Joshua was the world’s premier heavyweight. Ruiz outwitted everyone by landing several powerful punches that put Joshua to sleep – showing he was indeed the superior fighter on this particular evening and not just lucky.

Corrie Sanders Knocks out Wladimir Klitschko.

Sanders entered this fight as an unknown, while Klitschko appeared capable of dominating the heavyweight division for years to come. Instead, Sanders exposed Wladimir’s most notable weakness – his chin.

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