The Craziest Upsets in March Madness History

There are some March Madness betting trends that have become obvious over time. For example, most people should be aware that No. 12 seeds beat No. 5 seeds an impressive 35% of the time.

We also know that the No. 15 seed is 11-145 (.071) against the No. 2 seed, though there have been three of those upsets since 2021 alone with Princeton last doing it to Arizona in 2023.

Princeton STUNS Arizona and just like that, only 0.12% of brackets remain perfect. 😳 #MarchMadness pic.twitter.com/pwkKpGPrVN

— NCAA March Madness (@MarchMadnessMBB) March 16, 2023

But what about the mother of all March Madness upsets?

Three Shockers That Changed Basketball Forever

Since the NCAA tournament expanded the field to 64 teams in 1985, we get four No. 16 vs. No. 1 seed matchups every year, and they usually don’t go well for the huge underdogs with a 2-154 record, meaning they win 1.28% of the time.

But we wanted to highlight those two shocking upsets as they happened in the last decade and could be a sign of things to come. We also must never forget the impact the 1985 championship game had on this league and tournament.

UMBC vs Virginia: The 16-Seed Dream Comes True

It was always a statistical certainty that a No. 16 seed would beat a No. 1 seed someday. Some right combination of an underrated underdog and perhaps an overrated top seed with an injured star player, combined with some outlier shooting or favorable officiating could get the job done.

But what a shocker it was in 2018 when the UMBC Retrievers, a 20.5-point underdog, not only shocked No. 1 overall seed Virginia (31-2), but they stomped them by 20 points on their way to a 74-54 win.

The teams were tied at 21 at halftime before the Retrievers ran away with the game as Virginia allowed a season-high 74 points. UMBC was 12-of-24 from 3-point territory while the Cavaliers were just 4-of-22 (.182).

To Virginia’s credit, the team rebounded and won the national championship the next year. But someone had to be the first No. 1 seed to lose it to a No. 16 seed. UMBC lost in the second round to Kansas State and has not been back to the tournament.

Virginia entered today allowing 53.4 PPG.

It allowed 53 points in the 2nd half to UMBC. pic.twitter.com/8RW2cxuzei

— ESPN Stats & Info (@ESPNStatsInfo) March 17, 2018

FDU Takes Down Purdue: The 23.5-Point Underdog

Five years later, arguably a bigger upset happened when March Madness sleepers Fairleigh Dickinson upset Purdue for the biggest upset by point spread (23.5 points) in the NCAA tournament’s history.

Not only was FDU a No. 16 seed, but they were ranked last at No. 68 and played in the First Four tournament just to get to this game. They led 32-31 at halftime against Purdue, and the game went down to the wire with neither offense shooting 39% in the game.

Purdue had multiple chances to tie the game but was blocked on a layup and shot an airball on a 3. FDU held on before losing in the second round to Florida Atlantic.

Similar to Virginia in 2018-19, Purdue shook off the embarrassing loss and reached the national championship game in 2024. However, they lost in a blowout to Connecticut.

Fairleigh Dickinson called their shot before they played Purdue 🔥🔥 pic.twitter.com/Ig9IZPypFs

— Complex Sports (@ComplexSports) March 18, 2023

Villanova’s Perfect Night: The OG Championship Upset

Let’s never forget one of the greatest upsets in college basketball history in 1985 when the No. 8 Villanova Wildcats upset the No. 1 Georgetown Hoyas, who were looking to repeat behind center Patrick Ewing.

Both members of the Big East, Villanova, and Georgetown met twice earlier that season with the Hoyas winning 52-50 and 57-50, so the seeds were planted for the 9-point underdog to figure things out in the championship game.

It’s called “The Perfect Game” for Villanova after setting a Final Four record by shooting 22-of-28 (.786) from the field in a 66-64 upset. If that sounds like few shot attempts, it’s because Villanova took advantage of the no-shot clock in college basketball by running “four corners offense” and holding the ball for long stretches of time, an effective underdog strategy.

Villanova remains the lowest seed (No. 8) to win the men’s championship. Immediately following the win, the NCAA instituted a 45-second shot clock for the 1985-86 season.

Today is the 35th anniversary of Villanova beating Georgetown to win the 1985 NCAA Tournament title.@NovaMBB was an 8 seed, still the lowest seed to win a championship.

The Wildcats shot 78.6% from the floor, the best ever in a National Championship game. pic.twitter.com/lkYK5F74Lw

— ESPN Stats & Info (@ESPNStatsInfo) April 1, 2020

Who Is Cinderella in 2025?

The March Madness 2025 tournament will start next month, but be sure to keep up with the latest March Madness odds to see which teams might be poised for an upset this time.

Duke (19-2) and Auburn (20-1) currently have the best odds (+380 at BetUS) to win the championship, but you never know when a small-school Cinderella might come up with a different story.