March Madness has witnessed numerous shocking upsets that captivated sports fans worldwide, with several historic moments standing out as the greatest. Most famously, the University of Virginia Cavaliers suffered a stunning defeat when they became the first-ever number-one seed to lose to a sixteenth-seeded opponent, the UMBC Retrievers, by twenty points. Other legendary Cinderella moments include 1985 eight-seed Villanova defeating Georgetown for the title, and fifteenth-seed Florida Gulf Coast's electrifying run to the Sweet Sixteen, forever defining the unpredictable magic of the tournament.