Boxing's Greatest Upsets: Shocking Moments in the Ring

Boxing matches are always more exciting than any other sport. In every kind of sport, some moments and matches shock everyone from the industry. Likewise, there are plenty of moments in Boxing too. Among the many, we have brought up some of Boxing's most significant upsets in this article.

The seven astonishing boxing's greatest upsets are James "Buster" Douglas vs. Mike Tyson, Muhammad Ali vs. Sonny Liston, Michael Moorer vs. Evander Holyfield, Lloyd Honeyghan vs. Donald Curry, Max Schmeling vs. Joe Louis, Hasim Rahman vs. Lennox Lewis and Leon Spink vs. Muhammad Ali.

More than just having a fascination with a sport is required; you must know every twist and turn of the sport. If you are interested in Boxing, you cannot miss out on Boxing's greatest upsets in boxing history.

The Shocking 11 Boxing's Greatest Upsets 

Here are the 11 most astonishing boxing's greatest upsets in boxing history.

1 . James "Buster" Douglas vs. Mike Tyson (1990)

This match is one of Boxing's greatest upsets to date. The game took place in Tokyo Dome on January 11, 1990. James Buster Douglas is a 7-ranked heavyweight boxer with a massive physique known as Underdog. On the other hand, Mike Tyson is an undefeated greatest heavyweight boxer and champion.

The match lasted till the 10th round, with both the fighters battling and defending each other's power moves. However, in the last round, Douglas managed to land a nerve-wracking uppercut. It resulted in knocking out Tyson instantly. Nobody ever imagined this to be the ending of the match.

2. Cassius Clay (Muhammad Ali) vs. Sonny Liston (1964)

The legendary match between Muhammed Ali and Sonny Liston occurred on May 25, 1964. Did you know that Muhammed Ali's previous name was Cassius Clay? Well, if you did not, now you know. Another important fact about this match is that it contributes majorly to Ali's legendary career to boost up. 

Sonny Liston was a world heavyweight champion and thus an undefeatable fighter in his era. In the opposition, it was Muhammad Ali, a light heavyweight champion. The match was the most anticipated. However, to everyone's despair, Liston quit sitting on his stool before the beginning of the 7th round.

3. Michael Moorer vs. Evander Holyfield (1994)

The match between the biggest IBF heavyweight champions, Michael Moorer and Evander Holyfield occurred on April 22, 1994. Each fighter is highly dedicated, strength-bearing, passionate, and unbeatable in their track career.

Evander Holyfield (USA) vs Michael Moorer (USA) II | KNOCKOUT, BOXING  fight, HD - YouTubeImage source -

This match is quite different from all other boxing matches. Michael took the lead in the second round and managed to outbox Holyfield. This incident should have been a point scorer for Michael. However, Judge Jerry Roth scored it even and called it a draw. Later Michael with his claimed his victory to the jury.

4. Lloyd Honeyghan vs. Donald Curry (1986)

On September 27, 1986, Lloyd Heneyghan and Donald Curry played the most memorable match at Caesars Casino Hotel, Atlantic City. Curry hails from the United States, and Honeyghan hails from Britain. Both have several achievements in their divisions.

Curry is well famous in the US for his successful career. However, he and the crowd didn't take Lloyd Honeyghan as a formidable competitor, and that's why they took him for granted. Lastly, the undefeated Donald Curry was compelled to quit in the sixth round after bearing Homeyghan's aggressive and relentless attacks.

5. Max Schmeling vs. Joe Louis (1936)

The Boxing's greatest upset occurred between Max Schmeling and Joe Louis on June 19, 1936, at Yankee Stadium, New York. Max Schmeling was a lightweight and heavyweight champion from Germany. On the other hand, Loe Louise was a heavyweight Champion from the United States.

The match lasted till the 12 rounds, and Schmeling could successfully knock out Louis after massive aggressive attacks on Louis's face. The match was a huge upset because it was seen as a social and political conflict. It symbolized a struggle between democracy and fascism. 

6. Hasim Rahman vs. Lennox Lewis (2001)

The match between Hasim Rahman and Lennox Lewis, which took place on November 17, 2001, at Michelob Ultra Arena, is also considered one of Boxing's greatest upsets. Both fighters played in the heavyweight division, and both had their own set of achievements. 

Greatest Knockouts in Boxing History: 15. Lennox Lewis Vs Hasim Rahman 2 -  Fight Game Media

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However, Lennox Lewis had the upper hand initially as he was a heavyweight world champion fighter. The match lasted around 4 rounds, and Lewis successfully all the first three rounds. While in the fourth round, Lewis's famous left-right move made him the winner. Rahman tried to get up after the hit but collapsed at the referee's 9 countdown.

7. Leon Spink vs. Muhammed Ali (1978) 

This legendary match turned into another of Boxing's greatest upsets. The match was between the Olympic gold medalist Leon Spink and "The Greatest" Muhammad Ali. It occurred on February 15, 1978, at the Hilton Hotel Las Vegas. Undoubtedly, everyone has very anticipated this match cause it was between the bests.

Boxer Leon Spinks, Who Toppled Muhammad Ali, Dies At 67 | WKMS

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Ali was trying to make a hat trick by winning this fight, but that dream went to waste after Lewis's victory. Lewis's extreme passion, determination, and aggressive moves boosted his luck against fighting the undefeatable player. Ali's loss was not expected by anyone and had caught everyone off guard. This was indeed Boxing's greatest upset that shook the boxing industry.

Where to Stream Free Matches

What becomes essential after gaining knowledge about Boxing's greatest upsets is how to watch the upcoming matches. Witnessing the shocking matches is always exciting and will give you enough experience to gain the liberty to talk about it in public. If you were trying to find any source to watch free matches, then Sportsurge is all you need. 

Our platform lets you watch live matches in real time, especially with no annoying ads. Moreover, this source is not only confined to Boxing. You can also stream sports like NBA, NFL, MLB, NHL, MMA, Boxing, Formula, Soccer, Fomula1, XFL, Cricket, NCAA, CFB, WWE, and Golf with the help of Sportsurge.


Q. Which fight is still today considered Boxing's greatest upset?

Ans: The January 11, 1990 fight between James "Buster" Douglas and Mike Tyson is considered Boxing's greatest upset.

Q: What happened at the fight between Cassius Clay and Sonny Liston?

Ans: The first fight between Cassius Clay (Muhammad Ali) and Sonny Liston occurred on May 25, 1964, and Liston quit the fight after the 7th round.

Q: How did Max Schmeling's and Joe Louis's fight become upset?

Ans: On June 19, 1936, the fight between Max Schmeling and Joe Louis occurred. It became one of Boxing's greatest upsets due to its social and political conflict.


Boxing is almost everyone's favorite; even if not, people will not stop watching it. The sport's unpredictability and the toppling of traditional players by the new generation's strengths make the sport interesting. Some of the fantastic matches also shook the boxing industry.

The matches become nerve-wracking and named Boxing's greatest upsets, and we have talked about 7 of them in this article. These matches are important for boxing fanatics. The bonus information we tried to provide is how to stream free, ad-free matches. I hope all this information was fruitful to you.