The 2023 NCAA Tournament produced arguably the biggest upset in the event's history with 16-seed Fairleigh Dickinson stunning 1-seed Purdue in the first round. Upsets have always been a part of March Madness, but now teams with longer and longer odds seem to be doing the impossible. The Knights, who got into the Big Dance on a technicality and were the smallest team in Division I, outmuscled the Boilermakers to pull off the biggest upset by point spread in tourney history. 

While FDU was not the first 16 seed to take down a 1 seed, the list of such teams to pull off the seemingly impossible is fairly short. So short, in fact, that you can compile such upsets into a tight list. Those outcomes are a huge part of what makes the NCAA Tournament so great. Without them, March Madness would be less mad. Every once in a while, a game comes along early in the tournament and unfolds how few would predict. Of course, there's the Holy Grail -- a No. 16 seed beating a No. 1 seed, something that has now only occurred twice. 

Even if the early upsets ruin your bracket, it's still exhilarating. 

Below are the 10 craziest, most bracket-busting upsets the first weekend of the tournament has ever produced.

10. (15) Coppin State defeats (2) South Carolina, 78-65

March 14, 1997

Coppin State's depth was a huge reason for this upset. The Eagles bench outscored the Gamecocks' reserves 40-17. Danny Singletary led the way with 22 points. Two Coppin State starters didn't even score in 10 minutes of playing time and neither team shot well from beyond the arc. Coppin State was 2 of 13 and South Carolina hit 4 of 20 from beyond the arc. Coppin State jumped ahead late in the game after trailing throughout, but down the stretch they looked like a team that had been leading all day. Coppin State just looked faster than South Carolina, and went to the line 34 times to South Carolina's 16. It was a huge upset of the SEC champs and an abrupt end to their first tournament appearance since 1989.

9. (15) Richmond defeats (2) Syracuse, 73-69

March 14, 1991

Once again, we get to the first time one of these major upsets occurred. The Richmond Spiders were making their fifth appearance in the NCAA Tournament. Syracuse, on the other hand, was making its ninth in a row under Jim Boeheim. The Orange had better scorers -- and it showed -- with Billy Owens leading everyone with 22 points. Bench play, a running theme on this list, was the difference. Syracuse got just three points from its reserves and Richmond was able to outlast the Orange in a massive, unprecedented upset.

8. (15) Florida Gulf Coast defeats (2) Georgetown, 78-68

March 22, 2013

Florida Gulf Coast not only managed to take down Georgetown, but they went on to beat the No. 7 seed San Diego State afterwards as well. The Eagles came into this game as a solid team, with three players averaging double digits and a 26-11 record. Georgetown boasted future NBA player Otto Porter. For the Hoyas, it was Markel Starks who stole the show, dropping 23 points. But Florida Gulf Coast had both Sherwood Brown and Bernard Thompson score 20-plus points en route to a 10-point win. The Eagles, nicknamed "Dunk City," became one of the most fun teams to watch the entire month. They dunked five times against Georgetown, including an exclamation point of an alley-oop within the final two minutes.

7. (15) Oral Roberts defeats (2) Ohio State, 75-72

March 19, 2021

Only eight times in NCAA Tournament history had a No. 15 seed defeated a No. 2 seed entering the 2021 event. Oral Roberts made it nine by defeating Ohio State 75-72 in overtime behind a legendary performance from the duo of Max Abmas and Kevin Obanor. The two combined for 59 points in the win, and the Golden Eagles weren't done there.

ORU went on to beat No. 7 seed Florida in the second round before getting eliminated in the Sweet 16. Both Abmas and Obanor played all 45 minutes of regulation and overtime and combined for 10 total 3-pointers. Abmas was the nation's leading scorer entering the game and already known to some for his ability to rack up points. But the game marked a true breakout for Obanor, who went on to transfer to Texas Tech after the season.

6. (15) Santa Clara defeats (2) Arizona, 64-61

March 18, 1993

A point guard named Steve Nash came off the bench for Santa Clara in this one. However, while he had a solid game, he wasn't Santa Clara's ace in the hole. Nash scored 10 points, hauled in seven rebounds and notched four assists. Pete Eisenrich scored 18, leading the way for Santa Clara despite a wild finish. Arizona's press was tough to break, but Santa Clara shot well enough at the line to hold on. Pac-10 Player of the Year Chris Mills was held to 19 points, and an Arizona team with six future NBA players was knocked out in the first round in Salt Lake City.

5. (15) Middle Tennessee defeats (2) Michigan State, 90-81

March 18, 2016

This game was a big part of the rise of ex-Ole Miss coach Kermit Davis. The Blue Raiders found themselves up against the No. 2 Spartans, led by Denzel Valentine. How did Middle Tennessee pull this win off? With scoring depth. This wasn't an example of a mid-major just moving the ball better or playing flawless basketball. MSU out-assisted Middle Tennessee 20-16, and had just four more turnovers. But all five Blue Raider starters finished in double digits, with Reggie Upshaw leading the way at 21 points. Middle Tennessee never really pulled away in this game, usually holding between a three and eight-point lead, but MSU simply couldn't stop the Blue Raider offense.

4. No. 15 Saint Peter's defeats No. 2 Kentucky (85-79)

March 17, 2022

This was an overtime thriller for the ages. It marked just the 10th-ever instance of a No. 15 seed beating a No. 2 seed, and the fact that it was one of the sport's giants on the losing end made it all the more memorable. Saint Peter's got a combined 47 points from guards Daryl Banks III and Doug Edert, marking a career high for Banks and the fourth 20-point game of Edert's career.

It was the first-ever NCAA Tournament victory for Saint Peter's, a private school of roughly 3,500 students in Jersey City, New Jersey. For Kentucky, the heartbreaking defeat meant the program would likely go at least four calendar years between wins in the Big Dance. The Wildcats missed the 2021 NCAA Tournament, and there was no NCAA Tournament in 2020, leaving a 2019 Elite Eight run as the program's last significant postseason success.

3. (15) Lehigh defeats (2) Duke, 75-70

March 16, 2012

This was the other major upset in 2012. Duke had a roster boasting eight future NBA players and looked primed to make a deep run. It was 27-7 overall and finished second in the ACC. But Lehigh, led by future NBA star C.J. McCollum showed that quality trumps quantity. He dropped 30 points in the upset as Duke was booted in the first round for the first time since 2007. Lehigh kept the game close at the half and held on to a small lead down the stretch for the win.

2. (16) UMBC defeats (1) Virginia, 74-54

March 16, 2018

One of the wildest upsets in tournament history not just because it marked the No. 16 seed beat a No. 1 seed, but because of the score. What in the world happened to the Cavaliers? Historically, nearly all of the 15 seeds that have won did so by the skin of their teeth. UMBC was utterly dominant over Virginia in a 20-point win. The first sense of "it's happening" came at halftime when the game was tied at 21. UMBC came out of the locker and proved that this was in fact going to happen. They dropped 53 points in the second half, nearly equaling Virginia's total for the game, and Virginia had no answer. The game snowballed, and Virginia ended up in the pantheon of disappointment, becoming not only the first No. 1 seed to lose to a No. 16, but doing so in absolutely brutal fashion.

1. (16) Fairleigh Dickinson defeats (1) Purdue, 63-58

March 17, 2023

For decades, no 16 seed was able to upset a 1 seed. Now, it's happened in the span of five years. While UMBC will always be the first to do it, there are a few indicators that Fairleigh Dickinson's monumental win over Purdue in the 2023 NCAA Tournament was even more historically significant. No, the Boilermakers were not the No. 1 overall seed like Virginia (the Knights were, however, the No. 68 team). And, no, the Knights didn't run them out of the arena with a five-point win. 

By pretty much every other metric, however, FDU's first-round upset was the biggest in NCAA Tournament history. It marked the largest upset by spread (23 points) and even by size: The Boilermakers ranked as the No. 1 team in adjusted height, according to KenPom, while the Knights ranked dead last in Division I. It was as close to a David vs. Goliath matchup as they come. FDU also arrived to the Big Dance on a technicality, having lost to Merrimack in the NEC Tournament title game; however, because Merrimack is still transitioning to Division I, it was ineligible for the NCAA Tournament. Instead, the automatic bid went to the Knights.