Virginia’s 74-54 defeat at the hands of the University of Maryland, Baltimore County, was a long time coming.

It was the first time a No. 16 seed had beaten a No. 1 seed since the Division I men’s tournament expanded to 64 teams in 1985 — that is 33 years and 136 matchups of 16 versus 1. The loss on Friday was also embedded in the very way that Virginia has played basketball under Coach Tony Bennett for the better part of the past decade.

There may not have been a better regular-season college basketball team over the past five years than Virginia. Its 129 wins before the Atlantic Coast Conference and N.C.A.A. tournaments are among the best in Division I. That figure is the highest in the brutal A.C.C., and Virginia has won three of the last five regular-season conference titles.

But in the N.C.A.A. tournament, the Cavaliers have underperformed. As a top seed in 2014, they lost to fourth-seeded Michigan State in the round of 16. The next year, as the highest-ranked No. 2 seed, they fell in the second round. As a No. 1 seed in 2016, they suffered a fall-from-ahead loss to 10th-seeded Syracuse in the round of eight. When they lost in last year’s second round as a No. 5 seed, it was the first time in this span that they had not actually been upset in the tournament.