23. Cleveland State vs. Indiana (1986)
The Hoosiers had a great opportunity to progress to the second round in 1986. They received an easy matchup against Cleveland State. Or at least that’s what it seemed like on paper but their opponents had other ideas. In the end, this March Madness clash ended in humiliation for Indiana.

Bobby Knight’s team suffered a first-round exit for the first time in the celebrated coach’s career. It was an acrimonious ending to a tournament where they had high hopes. But the 83-77 scoreline didn’t flatter Cleveland, who earned the victory (via The News-Herald).