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The 25 Biggest Upsets in March Madness History

This is already the upsettiest tournament in NCAA history, but do any of these 2021 upsets rank among the top 25 Cinderella wins all time?

Brandon Anderson
SportsRaid
Published in
13 min readMar 24, 2021

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WHAT A WILD AND WONKY RIDE THIS 2021 MARCH MADNESS HAS BEEN. We’ve only played one weekend of basketball, and already this tournament has more upsets than any in modern NCAA tournament history.

If you consider an “upset” to be any win by a team seeded five or more spots below a favorite, we’ve already seen a 12 upsets in this year’s tournament, one more than the all-time record. And we may not be done yet! We’ve still got 11-seed UCLA up against 2-seed Alabama, and 2-seed Houston will have two chances for an upset loss, against 11-seed Syracuse first and then 8-seed Loyola Chicago or 12-seed Oregon State after that. And we haven’t even mentioned Oral Roberts, the second 15-seed ever to make the Sweet 16.

No tournament has seen more upsets than our 2021 March Madness, but have we really had that one huge, memorable upset that ranks up there with the all-time great Cinderella stories?

Think three years ago, when it finally happened. After 135 straight games of 16-seeds coming up short, we finally saw our first 16v1 upset when Maryland Baltimore County (UMBC) took…

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Brandon Anderson
SportsRaid

Sports, NBA, NFL, TV, culture. Words at Action Network. Also SI's Cauldron, Sports Raid, BetMGM, Grandstand Central, Sports Pickle, others @wheatonbrando ✞