Yes a number 16 seed has beat a number one seed in the NCAA Basketball tournament, but it was in the womens' tournament. In 1988, 16th seed Harvard beat 1st seed Stanford in the womens' tourney. (Answer by Mymomisnfat)
It also happened in 2018 when the University of Maryland - Baltimore County (16th seed in the South) beat the University of Virginia (1st seed in the South) by a score of 74 - 54.
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Yes,In 1998 in the NCAA Division I Women's Basketball Tournament 16 seed Harvard beat 1 seed Stanford
No. No 16th seed has every won the tournament or even won their first game. The lowest seed to ever win the championship is a #8 seed.
It's happened once before when NCSU won in 1983, making the prior probability 4.2%.