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Top 5 Biggest March Madness Upsets in History

March Madness annually is both one of the most thrilling sporting events in the calendar, as well as one of the most stressful and, at times, some might say unfair to bet on.

Every year, once the NCAA men’s basketball brackets are announced, college basketball pundits all around start their scheming, planning and of course thorough selecting which teams to back in the NCAA Tournament.

Top 5 Biggest March Madness Upsets in History
The UMBC Retrievers bench reacts to their 74-54 victory over the Virginia Cavaliers | Streeter Lecka/Getty Images/AFP

As funny as it may sound, at times it seems as if one of the most important components of the tournament is completely forgotten as soon as the March Madness brackets are announced.

Which, you may be asking?

The ever-so-dreaded but never-absent March Madness upsets.

Those games where overwhelming favorites get their hopes and dreams crushed by lower-level schools who are riding their very own “Cinderella Story” types of seasons and end up pulling off some of the biggest college basketball betting upsets.

While we prepare for the 2024 March Madness tournament, let’s look back at the top five biggest NCAAB Tournament upsets in history.

If your team is there, well, sorry.


1. UMBC 74, Virginia 54 (2018 First Round)

While I wanted to start the list off with last year’s No. 16 seed vs. No.1 upset, who would I be if I didn’t pay proper homage to the first-ever 16 vs 1 upset?

Back in the first round of the 2018 March Madness tournament, the No.16 UMBC Retrievers – yes, just like the dogs – stunned the No. 1- ranked Virginia Cavaliers. Not only did they knock the Cavs out of a competition where they were clear favorites to go all the way to the finals, they did it by 20 points – as 20.5 point underdogs according to the March Madness point spread.

To put it all into an even tighter perspective, we’re talking about a Virginia team that prior to that game had only lost two games that season by eight points total. Meanwhile, UMBC had fallen by 44 points to Albany.

It was a great day for the Retrievers, for owners of golden retrievers and basically for anybody not betting on Virginia.


2. Fairleigh Dickinson 63, Purdue 58, 2023 First Round

Now that we covered the first ever 16 vs 1 upset, let’s run that scenario back from last season when No.16 Fairleigh Dickinson knocked out No. 1 Purdue in the first round of the tourney.

I don’t even know what’s worse here. The fact that the FDU Knights in theory shouldn’t have even been in the tournament, or the fact the Boilermakers – 23.5 point NCAAB betting lines favorites – didn’t think for even a second that the Knights could end up winning this game.

FDU managed to squeeze its way into the tournament thanks to Northeast Conference champion Merrimack being ineligible to participate because of their transition from Division II to I. Yet, even after shooting ever so poorly during the vast majority of the game, the Knights managed to put on one of the strongest late-game runs in last year’s competition to beat Purdue by five points.


3. Villanova 66, Georgetown 64, 1985 National Championship Game

Yes, there once was a point where the Villanova Wildcats were not the powerhouse basketball school that has become a perennial March Madness predictions darling. Back in 1985, Villanova squeezed into the NCAA basketball tournament by the skin of its teeth and managed to put on the greatest – and yes, there’s no debate here – Cinderella story in college basketball history.

Squaring off against the Georgetown Hoyas, the March Madness odds who just happened to be defending champions, the Wildcats put on a shooting clinic, hitting an impressive 78.6% from the field that night.

Even if that was the last game in NCAAB history to be played without a shot clock, that still doesn’t take away from the fact the Wildcats pulled off one of the most important upsets in basketball history.


4. George Mason 86, Connecticut 84, 2006 Regional Final

I’ll keep this one short and sweet because, even if it happened almost 18 years ago, there’s no reason to why anybody should forget 2006’s George Mason basketball team.

The 11th-seeded Colonials take out No. 6 Michigan State, No. 3 North Carolina and No. 7 Wichita State on route to an Elite Eight berth. Once there, facing off against No. 1 UConn, George Mason had one of those proverbial “Yes, We’re Them” kind of moments that make sports ever so magical and stunned the March Madness prediction world by knocking out the heavily favored Huskies to make it to the Final Four.

It was the first time a small conference school had made it so far into the competition since 1979, and it will always be an upset worth remembering.

Take A Look At These Other 2 NCAAB March Madness Special Articles

5. Duke 79, UNLV 77, 1991 Final Four

Every time a conversation sparks about which teams are considered the best ever to never win a March Madness championship, the 1990-91 UNLV Runnin’ Rebels are always either number one or in the top three of teams in that list.

Yes, they had won the title the previous year, but come on, we all know the 1990-91 team was one of the best to ever set foot on the court – even better than the 1990 title winning squad.

I personally will always have a soft spot for the “Runnin´ Rebels.” Larry Johnson, who would go on to become a Charlotte Hornets and, above all, a New York Knicks legend. Yes, I’m a diehard Knicks fan, but Johnson was the leader of a team that could have been too good for their own sake.

Now, yes, it’s not every day you consider a No. 2 beating a No. 1-ranked team an upset. But considering UNLV had a perfect 34-0 record and destroyed the Duke Blue Devils the year before by 30 points in the NCAA tournament title game, Duke´s Final Four win against UNLV the following year ends up making the list.


5. NC State, 54 Houston 52, 1983 National Championship Game

What, a tie for fifth place? Yes, a tie for fifth place. When you have a game like 1983’s national title game between the North Carolina State Wolfpack and the Houston Cougars – aka one of the most dramatic in college basketball history – how can you not include it?

Nobody gave NC State a chance in the finals, especially against the heavily favored Cougars, with their high-octane “Phi Slamma Jamma” offense. The Wolfpack finished the game and sealed the March Madness title win with an alley-oop to cap the historical upset that will forever be engraved as one of the most drama-filled title runs in history.

College basketball lines are heating up. Bet on March Madness and see if you can be the champion!

Questions Of The Day

When Does The 2024 March Madness Tournament Begin?

The 2024 March Madness Tournament is set to start on March 19.

Which Team Could Be This Year’s Cinderella Story Squad?

The Grand Canyon Antelopes, a team whose March Madness betting odds stand at +25000, are looking like the team with the biggest Cinderella Story potential this season.

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