Since its first iteration in 1939, the NCAA DI men’s basketball tournament has given fans some of the most entertaining, triumphant moments in college sports. Because anything can happen during March Madness, it has also featured heartbreaks, maddening mistakes, frustrating officiating and anticlimactic match-ups that have distressed and disappointed fans so much that they talk about these incidents decades later. These 20 moments are the worst of the worst.

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