When Leicester City pulled off the greatest sporting upset in history by winning the 2015-16 Premier League at 5,000-to-1 odds, several visionary fans secured legendary payouts. Notable winners included a supporter who cashed out a £20 each-way bet early for a profit of over £108,000, another fan who collected roughly £20,600 from a modest £5 stake after partial cash-outs, and others who let their tickets ride to claim tens of thousands of pounds. These monumental windfalls cost bookmakers millions collectively, making it the most famous and costly long-shot payout event in the history of the sports gambling industry.