Biggest Upsets in Sports Betting HistorySports are unpredictable by nature, and that’s part of what makes them so thrilling—especially when betting is involved. Every now and then, a massive underdog triumphs against all odds, leaving fans in awe and bookies scrambling. These moments can be legendary for those who backed the upset and painful for those who didn’t. For bettors, these stories aren’t just entertaining—they’re full of valuable lessons.