While historical sports debates feature several legendary underdog triumphs, UMBC's historic 20-point victory over Virginia in 2018 stands universally recognized as the greatest upset in March Madness history. As a 16-seed facing a powerhouse 1-seed, the Retrievers shocked the sports world with a dominant second-half performance, securing the first-ever victory by a sixteenth seed over a top seed in the men's NCAA tournament and etching an unforgettable milestone into college basketball lore.