3 of the Biggest Upsets of the 21st Century


Despite requiring plenty of brute strength and endurance, boxing tends to ignite emotion within spectators. From the outside, the sport may look more like high-stakes dancing than a fight that lasts twelve rounds or until a knockout.

Whether fans are watching an overhyped faceoff between Mayweather and McGregor or a nail-biter between Wilder and Fury, the sport is rewarding for spectators. As pundits keep a lookout for impressive combinations or tell-tale signs of exhaustion, the action continues for round after round.

When it comes to studying stats and finalizing betting predictions for boxing (or any sport), there’s typically a clear favorite and underdog. Though boxing matches with close margins of talent are exciting and unpredictable, there are few spectacles as unforgettable as watching an underdog defy the odds.

Boxing is a sport that provides endless action that can shift momentum at the drop of a dime in the tenth round. Even if a boxer consistently loses every round, there’s still a chance he may come back for that end-all knockout that sees him walk away the champion.

The past twenty years have delivered a handful of unforgettable upsets. Some of the most notable underdog wins are listed below.

Lennox Lewis v. Hasim Rahman, 2001

Heading into the 2001 ‘Thunder in Africa’ fight between Lennox Lewis and Hasim Rahman, some Las Vegas sportsbooks refused to charge site fees because the match was expected to be a wash in favor of Lewis.

In fact, Lewis was more focused on the possibility of a superstar showdown against Mike Tyson than the match against Rahman. While Rahman headed to Brakpan, South Africa to acclimate to the altitude, Lewis shot a cameo for Ocean’s Eleven in Las Vegas.

The fight lasted five rounds before Rahman delivered a righthanded blow that dropped Lewis, who was unable to get back to his feet before the count ended. In the aftermath, Rahman became an overnight sensation with multiple offers from broadcasters.

Antonio Tarver v. Roy Jones, 2004

Billed as a ‘More Than Personal’ boxing match, Tarver and Jones had a charged history that lent to the excitement around the 2004 faceoff. In their original 2003 faceoff, Tarver faced a weakened Jones, who had recently dropped 25 pounds to re-enter the light heavyweight division.

Despite this, Jones won the first match and was the heavy favorite to win the pair’s rematch fight in May 2004. However, Tarver hung back as though observing Jones through the first round. In the second, a mistake by Jones saw Tarver land a quick left hook.

The hit dropped Jones for his second career knockdown. Though he stood before the count ended, the referee deemed him too hurt to continue. Tarver won by technical knockout, delivering one of the biggest surprise upsets since Buster knocked out Tyson.

Wladimir Klitschko

Marilyn Paulino/RBRBoxing

Wladimir Klitschko v. Lamon Brewster, 2004

Much like Buster Douglass mourned the passing of his mother before his fight with Mike Tyson, Lamon Brewster also faced the death of his trainer before taking out WBO champion, Wladimir Klitschko. At the time, such parallels didn’t affect Vegas sportsbooks, who favored Dr. Steelhammer.

Throughout the fight, Klitschko had the undeniable lead. The fourth round saw Brewster go down, but he roused his strength in the fifth round and began catching Klitschko off-guard. Right before the fifth round ended, Brewster sent Klitschko down.

Originally, the boxer stood and attempted to move toward his corner. However, the referee ended the fight. Brewster took away a TKO victory and the WBO belt. Klitschko was taken to the hospital, where it was determined his blood sugar was too high.

Though he eventually made a full recovery, the FBI conducted a full investigation to follow-up on claims that Klitschko had met with foul play prior to the match. There was no evidence to support this.

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