Five Major Boxing Upsets That Made Bettors Rich

Boxing fans love an underdog story, but nobody loves it more than the bettors who cash in on them. These five epic boxing upsets saw the odds stacked high, only for the favourites to crumble in the ring. Let’s dive into the fights that turned doubters into believers (and bettors into winners).

Memorable Boxing Upsets That Made Bettors Rich

Buster Douglas vs. Mike Tyson (1990)

In 1990, Mike Tyson was an unbeatable force. With 42-1 odds in his favour, Buster Douglas was expected to be just another name on Tyson’s win list. But on February 11, in Tokyo, Douglas delivered one of the most shocking knockouts in boxing history, knocking “Iron Mike” out in the 10th round. Anyone who placed a bet on Douglas that night laughed all the way to the bank. A $1,000 bet on Douglas would’ve made you an easy $42,000.

Andy Ruiz Jr. vs. Anthony Joshua (2019)

This upset was straight out of a Rocky movie. In 2019, Andy Ruiz Jr. stepped into the ring as a last-minute replacement to face the undefeated Anthony Joshua. With Ruiz clocking in as a 25-1 underdog, most fans thought the fight was over before it began. But by the seventh round, Joshua was down, and Ruiz stood tall as the new heavyweight champion. He earned the belts and made history as the first Mexican heavyweight champion. This fight was a perfect reminder for bettors that no fight is a sure thing.

Corrie Sanders vs. Wladimir Klitschko (2003)

Wladimir Klitschko was on the rise in 2003, and Corrie Sanders was not expected to pose much of a threat. With 40-1 odds against him, Sanders was expected to fold early. But in just two rounds, he sent Klitschko to the canvas four times, securing a knockout victory. Bettors who took the risk on Sanders cashed in big, while the Ukrainian had to rethink his entire strategy. It’s the kind of result that makes you question how predictable any match really is—and why some folks prefer to put their money on long shots.

Evander Holyfield vs. Mike Tyson I (1996)

When Holyfield stepped into the ring to face Mike Tyson in 1996, the betting odds were heavily in Tyson’s favour. Seen as past his prime, Holyfield was the underdog that the bookies loved to dismiss. But, in the 11th round, Holyfield stopped “Iron Mike” with a TKO, becoming the heavyweight champion again. This fight proved that experience, heart, and strategy could topple power. Bettors who ignored the hype and believed in Holyfield’s tenacity walked away with serious winnings.

Hasim Rahman vs. Lennox Lewis (2001)

Lennox Lewis was the king of the heavyweight division in 2001, and Hasim Rahman was seen as little more than a tune-up fight. The odds? A staggering 20-1 in Lewis’s favor. But Rahman wasn’t playing by the script. In the fifth round, Rahman shocked the world with a devastating right hand that knocked the Brit out cold. Those brave enough to back Rahman raked in huge payouts, while Lewis had to return for a rematch to reclaim his title.

The Underdog Story Lives On

These five epic upsets prove one thing: never count the underdog out. Whether you’re checking the odds at onlinegamblingsa.co.za or just watching, boxing is the sport where the unpredictable is always possible. The next big upset is always just one punch away.