When Underdogs Defied the Odds: Biggest Upsets in Sports History The biggest upsets in sports history made oddsmakers look foolish, underdogs famous, and bettors rich. In this blog, we’re diving into the shocks that flipped the script, busted a few bets, and reminded everyone that favourites don’t always get the memo. Key Takeaways: Even the biggest sporting giants have fallen to underdogs (e.g., Mike Tyson).