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Biggest Betting Upsets

The Biggest Betting Upsets in Sports History

Hassan Copeland, June 16, 2025

With the possible exception of those who backed the favorite, everyone enjoys an underdog story. In sports history, there have been times when huge underdogs won unexpectedly. These surprises changed the betting industry. While odds and stats can help, gamblers on sites like 22Bet know nothing in sports is certain. 

When heavyweight champion Mike Tyson and James “Buster” Douglas went off in 1990, it was one of the most well-known betting upsets. Tyson started the bout as a 42-to-1 favorite and was unbeaten and invincible. Douglas was seldom given a chance. Douglas shocked fans and made bookmakers pay big to those who backed the underdog. He knocked Tyson out in the tenth round, creating one of boxing’s biggest surprises. 

The third Super Bowl resulted in a historic upset in American football. When facing the much fancied Baltimore Colts, the New York Jets, led by quarterback Joe Namath, were overwhelming underdogs. Before the game, Namath famously promised victory, a daring claim that few people took seriously. He kept his promise by leading the Jets to a memorable win in NFL history, 16–7. 

Unforgettable Betting Upsets

Unbelievable results have also happened in horse racing. Mine That Bird, a horse with 50-to-1 odds, won the Kentucky Derby in 2009. The horse started at the rear of the group and won by over seven lengths thanks to an amazing surge in the last few miles. Both race spectators and wagerers were taken aback by the win, particularly those who had written Mine That Bird off as unlikely.

Soccer has delivered some unforgettable betting upsets, but few are as astonishing as Leicester City’s Premier League triumph in 2015–16. Starting the season as 5000-to-1 outsiders, Leicester pulled off what many considered impossible. Through gritty performances, team unity, and a few moments of brilliance, they turned a fairy tale into reality, lifting the trophy against all odds.

Tennis has had its share of shocks too. In 2009, Robin Soderling shocked everyone by defeating Rafael Nadal at the French Open. Nadal had never lost at Roland Garros before that match. Soderling’s win ended Nadal’s 31-match winning streak. It showed that even the strongest athletes can have weaknesses on big stages.

Stories like these are a powerful reminder of why sports captivate us. No matter how much data you study or how confident you feel, unpredictability is always part of the game. Underdogs will continue to rise, rewrite narratives, and leave bettors shaking their heads — and that unpredictability is what keeps the thrill alive, match after match.

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