The Greatest Betting Upsets in Boxing History

Boxing has enabled many bettors to make some serious money, with some making huge sums in some of the greatest betting upsets in boxing history. Perhaps one of the most famous is Muhammad Ali’s victory in The Rumble in the Jungle which came against all odds. As with most sports, boxing offers no guarantees to those who want to bet on the favourite, with Mike Tyson and Lennox Lewis also favourites that have been heavily defeated.

It is worth remembering that reports on odds for past games are not always accurate. With the advent of online casinos with sportsbooks, like 2, bettors can now be sure to find the best odds recorded. In the Douglas vs Tyson match discussed below, the posted odds on the fight reported odds going to 42/1 to bet on Tyson as the winner, though it was reported immediately after the fight that Douglas won as a 42/1 underdog, whose best odds were actually 37/1.

Jorge Linares first-round TKO to Pablo Cesar Cano
Jorge Linares was a -4500 favourite
In January 2019, Jorge ‘El Nino’ Linares from Venezuela recorded a shocking first-round loss against the hard-hitting Mexican, Pablo Cesar Cano. Linares was down three times before referee Ricky Gonzalez called a technical knockout with just a few seconds of the round left. The fight in New York destroyed Linares’ chances of fighting Maurice Hooker and gaining a world super lightweight title and was a sad way to mark his 50th professional bout.

James “Buster” Douglas knocks out Mike Tyson
The Odds: Tyson was a -4200 favourite
On 11 February 1990, James “Buster” Douglas scored a 10th-round knockout of Mike Tyson. Tyson had won his first title at age 21. His speed and punching power were intimidating to most and many boxers were anxious before even stepping into the ring.

Going into the match, Tyson appeared to be invincible over his previous 37 professional prizefights, whilst Douglas had four losses as a professional. On the day, nine rounds were evenly played until a vicious uppercut and sharp combination in round 10 left Tyson beaten.

Evander Holyfield TKO against Mike Tyson
The Odds: Tyson was a -2500 favourite
Mike Tyson and Evander Holyfield had one of the greatest boxing rivalries during the 1990s. In their 9 November 1996 fight, Tyson was demolished even though his four previous fights had seen him on top form. In contrast, Holyfield had lost two of his last four fights. Some boxing fans were even concerned for Holyfield’s life in this bout since there were concerns about a heart complaint.

Yet, from the start, Holyfield gave Tyson a pounding over 11 rounds before the technical knockout.

Andy Ruiz Jr. TKO against Anthony Joshua
The Odds: Joshua was a -2400 favourite
On 1 June 2019, Californian Andy Ruiz was a late stand-in against unbeaten WBA, WBO and IBF Heavyweight champion Anthony Joshua at Madison Square Garden. There were low expectations for the bout since it was just the second world title challenge for Ruiz. In addition, Ruiz had just a month to prepare. The low expectations may have worked in his favour, as Ruiz had nothing to lose yet proved to be faster, more aggressive and had more stamina. This means that Ruiz was able to recover swiftly from a knockdown in the third round to continue to fight against Joshua before the seventh round TKO.

Corrie Sanders TKO against Wladimir Klitschko
The Odds: Klitschko was a -2000 favourite
On 8 March 2003, Wladimir Klitschko was yet to know that he would go on to become one of the most successful heavyweight champions in boxing history. His WBO title defence against South Africa’s Corrie Sanders was not expected to be a challenge since Sanders had only boxed twice in three years before the bout. However, Sanders used his fast hand speed and strength over two brutal rounds that ended in a TKO.