In the history of the NCAA Division I Men's Basketball Tournament, a number one seed has been defeated by a sixteenth-seeded opponent on only two remarkable occasions. The first historic upset occurred on March 16, 2018, when the University of Virginia Cavaliers suffered a stunning defeat against the UMBC Retrievers by twenty points. The second monumental upset took place on March 17, 2023, when the Purdue Boilermakers were upset by the Fairleigh Dickinson Knights. These stunning shockwaves permanently shattered tournament brackets and remain etched in sports history as the ultimate David versus Goliath moments.