
The trick with winning your March Madness pool is to get your upset picks correct. It’s just that choosing which games to roll with as your upsets is a flip-on-the-coin task among even the most knowledgeable of college basketball fans.
Do you pick the classic 11-seed over 6-seed game? Maybe you’re feeling saucy and go with a 12- and 5-seed upset. Surely you won’t pick the 16-seed over the 1-seed, right?
It’s almost a guarantee that the upsets will happen, even if they’re, say a 5-seed over a 4-seed in the second round. In fact, the four 1-seeded teams have made the Final Four just twice in history, though once was, in fact last year, 2025. It was a notoriously few-upset season.
But chalk is boring. Let’s take a look at the years with the most upsets in the NCAA Tournament.
Note: For the purposes of this list, we’ll go with the NCAA’s definition of an upset. That is, an upset occurs when a team five seeds or more below its opponent wins the matchup.
Something was in the water coming out of the COVID pandemic. Twice has March Madness seen 14 upsets: 2021 and 2022.
In 2021, four teams seeded 12th or lower won their first round games:
By the time the Elite Eight rolled around, the Bruins and Beavers remained. UCLA ultimately made the Final Four, falling in overtime to the West’s No. 1-seed Gonzaga.
The next year went about the same way:
The craziest first round in NCAA Tournament history came just five years before the craziest tournament in history. In 2016, round of 64 saw eight teams pull major upsets.
It’s only happened twice, but those from another generation thought maybe that would never happen. But in 2018 and 2023, No. 16 Maryland Baltimore County beat No. 1 Virginia (by 20 points, no less) in ‘18 and No. 16 Fairleigh Dickinson beat No. 1 Purdue, a team that’s appearing here on the wrong end often.
Go just one seed lower, or higher, depending on your perspective, and a 15-seed has beaten a 2-seed on 11 different occasions. Most recently, No. 15 Princeton beat No. 2 Arizona in 2023 and the first came in 1991 when No. 15 Richmond beat No. 2 Syracuse.
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