Greatest Upsets in Boxing From the Last 40 Years: Douglas vs. Tyson, Ruiz Jr. vs. Joshua, and 12 More

Everyone loves a good underdog, especially when it comes to combat sports. Upsets are what make people stick around longer for the excitement. Since boxing's proliferation, there has been no shortage of upsets. Here, we take a look at the greatest upsets in the boxing history of the last 4 decades.

Kirkland Laing def.
Roberto Duran

Laing was a huge underdog as his record stood at 23-3-1 while Duran’s was 74-3. However, Laing shocked the great Roberto Duran on September 4, 1982, by winning this fight via a split decision.

Michael Spinks def.
Larry Holmes

Then undefeated (48-0) and the reigning IBF and The Ring heavyweight champion, Holmes was a heavy favorite. However, the underdog Spinks managed to upset the champion by a unanimous decision victory on September 21, 1985.

Iran Barkley TKO's
Tommy Hearns

Hearns was the WBC Middleweight Champion and the clear favorite when he took on Barkley on June 6, 1988. However, Barkley stunned the world by stopping Hearns in just three rounds.

Buster Douglas KO's
Mike Tyson

Douglas was a staggering 42-to-1 underdog against Tyson back on February 11, 1990. Moreover, Tyson was coming in undefeated (37-0)  into this fight. However, Douglas pulled one of the biggest upsets in heavyweight boxing history by knocking out Tyson in the tenth round.

Michael Bentt KO's
Tommy Morrison

On October 29, 1993, Morrison was a heavy favorite and was on a ten-fight win streak. Moreover, he was the reigning WBO heavyweight champion, a title he claimed by defeating George Foreman. However, the entire world got shocked as the underdog Bentt claimed a first-round KO victory over Morrison.

Frankie Randall def.
Julio Cesar Chavez Sr.

Chavez Sr. was on a 90-fight unbeaten streak (89-0-1) and was expected to walk over Randall on January 29, 1994. However, Randall shocked the world as he dropped Chavez Sr. in the 11th round and eventually won the fight via a split decision.

George Foreman KO's
Michael Moorer

On November 5, 1994, then-undefeated (35-0) Moorer was a heavy favorite, who was also coming off defeating Evander Holyfield. Moreover, Foreman was a 45-year-old coming into this fight. However, Foreman stunned the world by claiming a spectacular tenth-round KO victory.

Oliver McCall TKO's
Lennox Lewis

Then undefeated (25-0) Lewis was expected to obliterate McCall on September 24, 1994. However, McCall pulled one of the biggest upsets by defeating Lewis via TKO in just two rounds.

Evander Holyfield KO's
Mike Tyson

Holyfield was a 25-1 underdog against Tyson, who was on an eight-fight win streak and the reigning WBA heavyweight champion on November 9, 1996. However, Holyfield defied the odds by stopping Tyson in the 11th round to become a three-time heavyweight champion.

Hasim Rahman KO's
Lennox Lewis

Lewis was on a fourteen-fight win streak and the reigning WBC, IBF, and IBO heavyweight champion on April 22, 2001. However, the underdog Rahman unleashed a thunderous overhand right and dropped Lewis in the fifth round.

Corrie Sanders TKO's
Wladimir Klitschko

Klitschko was 40-1 and looking to make his sixth defense of his WBO heavyweight title on March 8, 2003. Moreover, the champ was on a 16-fight win streak. However, the underdog Sanders stunned the world as he claimed a second-round TKO victory over Klitschko.

Tyson Fury def.
Wladimir Klitschko

Despite being undefeated (27-0), Fury was coming into the fight as an underdog. Moreover, Klitschko was on a magnificent 22-fight win streak. However, Fury managed to upset Klitschko via a unanimous decision on November 28, 2015.

Jeff Horn def.
Manny Pacquiao

On July 2, 2017, the all-time fan-favorite Manny Pacquiao was coming into the fight after defeating two elite boxers, Timothy Bradley and Jessie Vargas. He was expected to walk over Horn. However, Horn managed to pull a unanimous decision victory over the boxing legend.

Andy Ruiz Jr. TKO's 
Anthony Joshua

On June 1, 2019, Ruiz Jr. pulled one of the biggest upsets in heavyweight history as he knocked Joshua down four times en route to a seventh-round TKO victory. This upset flipped the state of the heavyweight division upside down as Joshua was expected to defeat Ruiz Jr. and eventually go up against Deontay Wilder.

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