For every Cinderella, there is a team that tastes disappointment.
That's what makes the big upsets so dramatic, especially in the NCAA tournament, where meek mid-majors and fiery upstarts enter the field with nothing to lose and a pocket full of house money. This holds true in the later rounds as well, where blue bloods with an air of destiny meet face-to-face with hot-shooting spoilers.
College hoopheads are familiar with the short list of great March Madness upsets. But what about the other side of the coin? Probably less so. That's why we're here. Own your next debate with this list of the NCAA men's tournament's most devastating losses.
10. Weber State outguns North Carolina (1999)
Expectations were slightly lower in 1999 compared with 1998, when Antawn Jamison and Vince Carter led the Tar Heels to the Final Four. But the cupboard was far from empty in Chapel Hill.
Even without Carter and Jamison the team held an air of celebrity, with future NBA player Brendan Haywood and a steady junior floor leader in Ed Cota. (Interestingly, this team also had a future NFL player on its roster in Ronald Curry.)
Fans and pundits widely expected heavily favored No. 3-seeded North Carolina to make a deep run, not to mention cruise to a first-round victory over No. 14 Weber State. But it was not to be.
No one had ever heard of Harold Arceneaux, and few have heard from him since. But in this game, he seemingly couldn't miss, draining 14 of 26 shots from the field en route to a 36-point performance and a 76-74 Weber State victory.
The following year, UNC was back in the Final Four, making 1999 a perpetual what-if.
9. The Adam Morrison Game (2006)
If you were watching live, it's hard to forget the image of Gonzaga star and Player of the Year candidate Adam Morrison crying into his feathery mustache as UCLA ran away with the glory.
The Bruins were seeded higher than the Zags, with the former clocking in at No. 2 and the latter at No. 3. Still, Morrison was a seemingly unstoppable scorer who could finally get that era's original mid-major Cinderella over the hump.
Behind Morrison's 24 points, the Bulldogs looked poised to move to the Elite Eight. In fact, they were leading by nine with roughly three minutes left. But Gonzaga appeared to take its foot off the proverbial gas, allowing UCLA to score the final 11 points to eke out a victory in a game Gonzaga fully controlled—right up until the waning seconds.
Morrison's emotional outpouring, which began before the game was even over, stands as an indelible example of tournament anguish.
8. Gritty West Virginia Stares Down Loaded Kentucky (2010)
The Kentucky Wildcats were beyond loaded, with 2010 No. 1 pick John Wall and big-time future pros like DeMarcus Cousins and Eric Bledsoe in the fold. What could their weakness possibly be?
Bob Huggins and the Mountaineers sniffed it out: It was behind the arc, where the Wildcats shot just 33.1 percent on the season. West Virginia has been a tough-minded defensive team ever since Huggins took over as head coach in 2007-08. This year was no different behind tournament darling Da'Sean Butler.
WVU held UK to 4-of-32 shooting from deep. For all you English majors out there, that's 12.5 percent. It spelled the downfall of arguably the most talent-rich Kentucky team in recent memory. And that's saying something.
7. Michigan State Stunned in Opening Round (2016)
Michigan State wasn't the flashiest team during the 2015-16 campaign, but the always-battle-ready Spartans were seen as a lock for the tournament's second weekend.
But then came the intrepid Blue Raiders of Middle Tennessee, which pulled off the 90-81 shocker to become only the eighth No. 15 seed to upset a No. 2 in the tournament.
That year, much of coach Tom Izzo's roster was comprised of seasoned seniors—just the way he likes it. Sparty entered the tourney on the two-line but were viewed as a trendy title pick thanks to a late-season streak in which they won nine straight and 13 of 14, not to mention a Big Ten championship.
The Blue Raiders jumped out to a 15-2 advantage, and MSU never seemed to regain its footing. When it came to nip-and-tuck, Michigan State had several significant miscues.
Star guard Denzel Valentine committed a key turnover in the game's final minutes with his team trailing 79-76—one of his six giveaways on the day. Missed shots and defensive lapses were frequent. This was a self-inflicted wound that unfolded over the course of the game, and it led to one of the biggest shockers in tournament history.
6. Maryland Coughs It Up vs. Duke (2001)
Playing in its first Final Four game in school history, the Maryland Terrapins were a No. 3 seed entering the game, while Duke was once again atop its bracket. So why is this 95-84 loss such a bad defeat?
With about seven minutes left in the first half, the Terps led the Blue Devils by 22 points and appeared to be poised to punch their ticket for the last game of the season.
It was not to be. Duke outscored Maryland 57-35 in the second half for the biggest comeback in Final Four history to advance to the national title game. The Blue Devils won that one too.
5. UCLA (Finally) Loses (1974)
Earlier in the 1973-74 season, UCLA's 88-game winning streak ended at the hands of Notre Dame, making that Irish team a factoid in sports trivia for the rest of recorded time.
NC State's accomplishment that season is not as well-known, even though it was even gaudier: The Wolfpack halted the Bruins' national title streak at seven with an 80-77 victory in the Final Four.
The immortal Bill Walton dropped 29 on the Wolfpack, but that accounted for nearly 38 percent of the team's points. On the other side, the perpetually unsung David "Skywalker" Thompson contributed 28 points and 10 rebounds to NC State, which went on to win the national title against Marquette.
4. The Chris Webber Timeout (1993)
This example is so gut-wrenching that it almost feels wrong call it out. But no list of devastating March Madness losses is complete without North Carolina’s 77-71 national championship victory over Michigan's talented but star-crossed Fab Five.
Webber went on to become a five-time NBA All-Star, but the phantom timeout still haunts his legacy.
Who can forget the image of Webber dribbling up the sideline and all the way to the corner, where he was promptly double-teamed. With 11 seconds on the clock and Michigan trailing 73-71, Webber called timeout, but the team no longer had any. That's a technical foul. Donald Williams sank both free throws to make it a two-possession game, and that was all she wrote.
3. Villanova Shoots the Lights Out (1985)
Nearly 79 percent.
That's the Villanova shooting percentage from this 66-64 shocker against the dominant Georgetown Hoyas. It was Patrick Ewing's senior season, back when top stars played four years and dominant big men were seen as unstoppable forces.
The No. 1 Hoyas were an eight-point favorite to handle the eighth-seeded Wildcats. With Ed Pinckney—Villanova's tallest player to see meaningful time—just 6'9" to Ewing's 7'0", the proceeding felt like a glorified senior day for Ewing as a coronation as the best college basketball player in history.
And then came the Wildcats' 78.6 percent shooting from the field. Dwayne McClain and Pinckney each shot 5-of-7. Harold Jensen went 5-of-5 off the bench. It was a crushing loss for Georgetown. And Ewing, fairly or not, earned a reputation as a star who couldn't win the big one.
2. UConn Shocks Duke (1999)
The Blue Devils were a 9.5-point favorite to complete their season of destiny and take their rightful place atop college basketball.
No one was arguing against it; it was just a matter of waiting for the inevitable.
After all, Elton Brand (16.2 points, 8.9 rebounds and 1.9 career blocks per game) was unstoppable. Here's an even more telling stat: in the 1998-99 season, Brand had a remarkable 10 win shares on the season. By comparison, the 2020-21 leader in that category, Luka Garza—who appears to be a lock for National Player of the Year—sits at 5.6, and Brand's mark is still in the top 10 for a single season.
Duke also had Shane Battier, a Greek god of drawing charges. Corey Maggette was a freshman phenom, and Trajan Langdon was a dead-eyed shooter back when shooting was still a specialist's game. Brand and those three combined for 47 seasons in the NBA.
Now, UConn was no slouch as a No. 1 seed with future pros Richard Hamilton and Jake Voskuhl on the roster. But as the odds indicate, no one expected them to compete with the Blue Devils.
Still, at the end, the Huskies were wearing the net like jewelry after a 77-74 victory. Hamilton led all scorers with 27 points, while the Huskies defense held the Devils to 41.1 percent shooting from the field and out-rebounded Duke 38-27. No Duke player besides Brand managed more than four boards.
Duke haters around the world rejoiced, but March 29, 1999, was a dark day in Durham.
1. UMBC Fells Virginia (2018)
How could the top spot belong to any other team?
The UMBC Retrievers began their first-round game on fire and stayed that way. As monstrous 20.5-point underdogs, it was clear they decided they had nothing to lose and to let it fly.
And let it fly they did, converting 12 of 24 three-point attempts. Virginia shot a lot of threes as well, but their numbers—4-of-22 for a dismal 18.2 percent—were underwhelming.
In the end, UMBC had pulled off the second-biggest point-spread upset since the NCAA tournament field expanded in 1985 and became the first 16th seed in men's tourney history to knock off a No. 1-seeded team.
Meanwhile, the Cavaliers team—nay, the program—appeared to be in tatters. After all, Virginia was pegged as a legitimate title favorite, typically clocking in below Villanova, who did go on to cut down the nets.
Ultimately, Virginia rose from the ashes and captured a national title the following season, but the moment of defeat in 2018 was about as bleak as it gets.