Let’s make this clear, the No. 1 most fascinating aspect of the NCAA March Madness tournament is the upsets. This month-long event is beloved by so many sports fans, not only to showcase the young talent headed to the NBA draft, but for the sheer intensity and dramatic circumstances these young aspiring players must endure, due to the win-or-go-home format. Dreams are made and crushed, and careers can spark or end here. When a come-from-behind victory happens in March Madness, it takes the dreaded feeling of loss to a whole new level. With plenty of upsets handed out almost every year, here’s a look back at the all-time biggest upsets NCAA history.

10. Texas Western Vs. Kentucky, 1966

In an era filled with racism, Texas Western became the first team to start five African American players. Despite having odd calls against them all game, they managed to dominate and take the championship from Kentucky. Later on, a film called Glory Road was made based on this historic event. This short documentary explains the whole situation well.

9. South Carolina (2) Vs. Coppin State (15), 1997

The Coppin State Eagles had never been relevant, coming in as a fifteenth seed in 1997. With South Carolina being seeded second, playing each other in the first round seemed like a huge mismatch, to say the least. Danny Singletary had other ideas, leading the Eagles past South Carolina 78-65, marking the first time Coppin State had ever won a game in NCAA tournament history. No dramatic buzzer-beater, just a total shocker of a result.

8. Weber (14) Vs. North Carolina (3), 1999

The Tar Heels had not lost a first round game in 19 years, while Weber hadn’t even qualified for the tournament since 1995. Fighting off North Carolina would be no easy feat. That is, until the game came apart in the middle of the second half for UNC. Thanks in large part to Harold Arceneaux, who dropped a game high 36 points, the 19 year streak of first round victories by North Carolina was officially over. Check out the final few minutes of the game in the video below.

7. Hampton (15) Vs. Iowa State (2), 2001

Iowa State, No. 2, led in 2001 by guaranteed first round draft choice Jamaal Tinsley, clearly had the edge over fifteenth seed Hampton. However with 6.9 seconds on the clock, Hampton’s Travis Williams gave his Pirates a late lead of 58-57. Iowa, with the 6.9 seconds left, had time for one last shot.  They had a great chance, on a lay up of all things.  But that ball just didn’t make it through the hoop. Who was the culprit? Yup, you guessed it. Jamaal Tinsley. Skip to 3:50 of the video below to watch the final few seconds.

6. Santa Clara (15) Vs. Arizona (2), 1993

Santa Clara was relatively unheard of, ranked as the fifteenth seed with no particular rising stars.  Meanwhile, Arizona had a future NBA star in Damon Stoudamire. Expected to roll over the Broncos, Arizona got into some serious foul trouble. Meanwhile, a no-namer you might have heard of, future two-time NBA MVP Steve Nash, nailed six straight free throws and Santa Clara became only the second fifteenth seeded team in NCAA history to win a game.

5. Duke (2) vs. UNLV (1), 1991

This was the beginning of the Blue Devils having sustained success in the tournament well into the 90s. The reason this was such a phenomenal upset? Well, UNLV came into the Final Four against the Blue Devils being praised as the tournament’s “Greatest Team Of All Time,” led by Larry Johnson. The Rebels were 34-0 coming in and also beat Duke by 30 the previous year for the title. However, in a game that featured multiple future NBA stars, it ended Duke 79 – UNLV 77.

4. Richmond (15) Vs. Syracuse (2), 1991

The Syracuse Orange has always been known as a great collegiate basketball titan, and in 1991 it was no different. They were seeded No. 2 and taking on the Richmond Spiders. This was meant to be a first round wash. The game itself wasn’t climatic, but was fairly close with a final score of 73-69. In the end, Richmond became the first No. 15 seeded team to ever win a game in tournament history, and knocked out the highly touted Syracuse.

3. Villanova (8) Vs. Georgetown (1), 1985

The Georgetown Hoyas were of an elite class in 1985, led by the deadly inside presence of Patrick Ewing. The Villanova Wildcats were not overly competitive against the Hoyas, until they met in the tournament in March. Villanova only missed a single shot the entire second half and ended up shooting 79% from the floor for the whole game, which set a new record in shooting percentage. In a game played before the 35 second shot clock was implemented, their patience paid off.  Villanova won 66-64.

2. Valparaiso (13) Vs. Mississippi (4), 1998

Valparaiso came in seeded No. 13, and Mississippi No. 4. On paper, maybe it was not a shock that the lower seed could prevail. After all, we’ve seen it happen before. However, the game’s conclusion hows why it was viewed with disbelief. With Valpo down 67-69 with four seconds left on the clock, Ansu Sesay of Mississippi missed two free throws, giving the Crusaders one last chance at victory. Jamie Sykes threw a hail Mary pass to Bill Jenkins just past midcourt, and Jenkins quickly found Bryce Drew, who was coming from behind him. Flailing the ball towards the rim at the last second, Drew drained the game winning 3-pointer that came to be known around the NCAA as “The Shot.”

1. N.C. State (6) Vs. Houston (1), 1983

Houston entered the tournament expecting to dominate, with future NBA stars Hakeem Olajuwon and Clyde Drexler on the roster. Conversely, North Carolina State barely qualified for the the NCAA tournament, having its ups and downs during the 1983 season. The Wolfpack hung in tough throughout, and the game was tied at 52 late. N.C. State had the ball with 44 seconds on the clock. Maintaining the ball for 42 of those seconds (again, pre-shot clock), with some questionably dangerous passes, the ball was in Derrick Whittenburg’s hands when he launched a three from well outside the top of the arch. As expected, it fell short. But it landed in the hands of Lorenzo Charles, on his way up to dunk it home at the last second. In the end, Olajuwon would go on to be named the tournament’s Most Outstanding Player, marking the last time a player on the losing team has ever taken home the honor.