March Madness is the best time of the year for sports fans. For 40 minutes at a time, storied programs like Kansas and Duke get on the biggest stage in the game with Cinderellas like Bucknell and Lehigh, and anything can happen.

But the nature of a tournament is that only one team can end the season happy. 68 teams have a chance to win it all after the bracket is revealed on Selection Sunday, but 67 of them will end their year with a loss. Some of these losses hurt worse than others. The four Division 1 programs in the state of Iowa know this as well as anyone.

Drake, Iowa, Iowa State, and Northern Iowa have enjoyed success in the NCAA Tournament. But they have also felt the agony of defeat in some of the worst ways.

I’ve attempted to take these bad losses and rank them to come up with which losses were truly the “worst.” Factors in this decision include how the game ended (buzzer beater?), how late in the tournament the game was, and how the team’s chances of advancing in the Big Dance were perceived at the time of the loss.

I intended this article to be a Top 10, but Iowans have simply experienced too much pain over the years in March. It is now a Top 12 with five honorable mentions.

So, join me for a trip down the saddest memory lane of basketball imaginable. We begin with number 12:

12. UCLA 85, Drake 82 – 1969 Final Four

If you’re like me, you didn’t know that Drake had ever played in a Final Four, let alone a game like this. In 1969, Drake won the Midwest Region and was paired with UCLA, the #1 team in the country, in the Final Four. UCLA was led by Hall of Fame coach John Wooden, future NBA guard Lucius Allen, and all-time great Lew Alcindor (now known as Kareem Abdul-Jabbar).

Drake hung close with UCLA and trailed by just 2 points at halftime. With 0:55 remaining in the game and UCLA holding onto a 9-point lead, the Bulldogs went on an 8-0 run to get the lead down to 1, but couldn’t get over the hump. Drake finally lost by 3.

This was by far the toughest test that UCLA faced throughout the 1969 tournament. Their next closest tournament game on the road to the national championship was a 15-point win over New Mexico State. Drake fans could hold their heads high after this one, but the “What might have been?” question is enough for this game to enter our list at #12.

11. #6 Minnesota 81, #14 Northern Iowa 78 – 1990 Round of 32

1990 marked the first March Madness appearance for Northern Iowa. They entered the tournament as a #14 seed playing 3rd-seeded Missouri. In a shocker, the Panthers knocked off the Tigers 74-71 thanks to Maurice Newby’s three-point shot with four seconds remaining and advanced to the second round.

UNI ran into Minnesota in the second round with a trip to the Sweet 16 on the line. After their stunning victory over Mizzou, some thought they could be a team of destiny to advance to the second weekend. The Panthers kept it close, but ultimately Minnesota proved too much to handle and won the game by three points. This is another example of a game that Northern Iowa fans can be proud of, but also wonder what might have been if they managed to pull it out.

10. #3 Idaho 69, #6 Iowa 67 (OT) – 1982 Round of 32

Iowa was a scorching hot team through much of the 1981-82 season, achieving an 18-2 (10-1) record and a #5 national ranking in mid-February. The Hawkeyes stumbled through the stretch, however, losing five of their last seven entering the NCAA Tournament.

Iowa received a 6-seed in the tournament and dispatched Northeast Louisiana (now Louisiana-Monroe) in the first round. This set up a showdown with the #3 seed Idaho Vandals.

Idaho led most of the way, but the Hawkeyes fought back and took their first lead of the game with about seven minutes to play. The Vandals missed a shot at the buzzer which send the game to overtime. Unfortunately for Iowa, the Vandals missing a buzzer-beater would not happen a second time.

With the score tied at 67, Idaho guard Brian Kellerman took a 15-foot jumper at the buzzer. The ball bounced high off the rim… bounced off the rim a second time… and finally dropped through to give Idaho the buzzer-beating victory and send Iowa packing.

9. #2 Ohio State 78, #10 Iowa State 75 – 2013 Round of 32

The Cyclones were hot as they entered their second March Madness game in 2013. Fresh off a dismantling of the #7 seed Notre Dame Fighting Irish, Iowa State hung close with Ohio State throughout the first half and entered the locker room at halftime trailing only by two points.

The second half remained close until the Buckeyes started to extend their lead about halfway through. With 6:00 remaining in the game, Ohio State led 69-56 and the Cyclones were on the ropes.

But this Iowa State team could score in bunches, and score they did. A Melvin Ejim three started a 13-0 run that got the score tied at 69 in just over two minutes of game time. Tyrus McGee scored the next six for the Cyclones and the upset was within reach.

With 1:41 remaining, Iowa State led 75-74 and had the ball. As Will Clyburn drove to the basket, Aaron Craft slid in and received a controversial charge call. After a tense 100 seconds of basketball that featured only one point, Ohio State held the ball for the last shot with the game tied at 75. Aaron Craft rose and fired a three over Georges Niang that gave the Buckeyes a trip to the Sweet 16. For Cyclone fans, this loss hurt just a little bit more as the 2012-13 team had experienced more than its fair share of close losses.

8. #3 Villanova 55, #7 Iowa 54 – 1983 Sweet 16

After Iowa’s brutal loss to Idaho in the 1982 tournament, the Hawkeyes were back for more the following year. This time, Iowa won both of its first two games, including a 77-63 upset of #2 seed Missouri, to advance to the Sweet 16.

The Hawkeyes dropped this game in one of the most frustrating ways: missed free throws. With two minutes to play and the score tied, Iowa’s Bob Hansen went to the line to shoot one-and-one. He missed the front end. After Villanova made two from the charity stripe, Iowa’s Greg Stokes was fouled. He made one of two to cut the Wildcat lead to one. But John Pinone made two more free throws for Villanova to extend the lead to 3 with 0:12 remaining and that turned out to be enough.

The loss to Villanova was Lute Olson’s final game as Iowa’s head coach. Days later, he accepted the Arizona job. Iowa’s 1983 tournament berth also marked the first time that a state of Iowa school qualified for March Madness in five consecutive seasons, setting a record that would last until Iowa State reached six consecutive tournaments from 2012-2017.

7. #15 Hampton 58, #2 Iowa State 57 – 2001 Round of 64

Entering this game, only three #2 seeds had ever lost to a #15 seed. Iowa State became the fourth. (That number now sits at eight entering the 2017 tournament.)

With a one-point lead and less than a minute to play, the Cyclones got a stop and inbounded the ball. Iowa State broke Hampton’s press and Jamaal Tinsley attempted a short-range floater that would have put Iowa State up 3. He missed, Hampton grabbed the rebound, and with 6.9 seconds left, Hampton forward Tarvis Williams hit a shot in the lane to give the 15-seed the lead. Jamaal Tinsley flew down the floor and got to the rim with another late chance to score and salvage a win, but he couldn’t get it to go.

Sixteen years later, “Hampton” is still a dirty word for many Cyclone fans because of this game. This abruptly marked the end of one of the best two-year stretches of Iowa State basketball in history, including two 2-seeds in the NCAA Tournament. Following this, in the ten seasons from 2002 to 2011, the Cyclones would only qualify for March Madness one time (in 2005).

6. #14 Northwestern State 64, #3 Iowa 63 – 2006 Round of 64

The 2005-06 Iowa Hawkeyes spent most of the season in the AP Top 25 and sprinted through the Big Ten Tournament to earn the automatic bid to the Big Dance. They received a #3 seed and became a trendy dark horse pick to do real damage in the tournament. But the Hawkeyes became the fifteenth 3-seed to lose to a 14-seed in NCAA Tournament history. (That number now stands at 21 entering the 2017 tournament.)

The Hawkeyes didn’t have trouble for much of the game. Iowa led by 17 points with 8:30 left to play. This was where the Demons began their run. With just under 15 seconds to play and Iowa clinging to a one point lead, Greg Brunner went to the free throw line to shoot two. He made the first and missed the second, setting up Northwestern State’s crazy finish.

The Demons came down the floor and launched a three. It missed, and the ball floated toward the corner. Jermaine Wallace came up with the ball and, with under three seconds to play, had no choice but to launch a contested three. Somehow it went, and Northwestern State took the lead. Adam Haluska had a chance at the buzzer, but missed, and the #3 seeded Hawkeyes were shockingly one-and-done.

5. #12 Western Kentucky 101, #5 Drake 99 (OT) – 2008 Round of 64

The 2007-08 Drake Bulldogs were just plain fun to watch. They put up points in a hurry. Led by first-year coach Keno Davis, former walk-on Adam Emmenecker, and Klayton Korver, the brother of current Cleveland Cavalier and former Creighton star Kyle Korver, the Bulldogs entered the NCAA Tournament with a 28-4 record and a real opportunity to introduce Drake University to the basketball world.

That opportunity was short-lived. #12-seed Western Kentucky came out hot in this first round game and took a 47-38 lead into halftime. But no lead was safe against this Drake team, and the Bulldogs put up 50 points in the second half to get the game into overtime at 88-88.

Overtime was back and forth. With 0:21 remaining and the Hilltoppers leading by one, Drake got to the rim and pulled down two offensive rebounds before forward Jonathan Cox was fouled. With six seconds left, Cox hit both at the line to give Drake a 99-98 lead.

Western Kentucky’s Tyrone Brazleton ran the ball down the floor and flipped it to Ty Rogers. With three Drake defenders in his face, Rogers nailed the NBA-range three point shot as the buzzer sounded to give the Hilltoppers the win. As of 2017, this is still the last NCAA Tournament game that Drake has participated in.

4. #2 UCLA 74, #6 Iowa State 73 (OT) – 1997 Sweet 16

The 1996-97 Iowa State team had high expectations. At one point, the Cyclones were the #4 team in the nation. While that ranking fell off by Selection Sunday, which slotted Iowa State as a #6 seed, the talent on the team was still just as capable of making an Elite Eight. But a heartbreaking loss to UCLA stopped Iowa State just short.

Iowa State led this game for most of the way, but UCLA came back to force overtime. The game remained close until the very end. With 11 seconds left and UCLA leading 72-71, Iowa State forced a turnover. Inbounding underneath the hoop, Jacy Holloway flipped an alley-oop to Shawn Bankhead for the Cyclones to take the late lead.

UCLA guard Cameron Dollar then came right down the court. Controversially, he used his arm to create space from Holloway, who was closely defending him. While Holloway fell to the floor, Dollar put a shot over Kelvin Cato off the glass and into the hoop with 1.9 seconds left. Iowa State committed a five-second violation while attempting to inbound the ball and UCLA took the win.

3. #1 Michigan State 75, #2 Iowa State 64 – 2000 Elite Eight

Just as “Hampton” is a dirty word for Iowa State fans, so is “blarge.” Mention that portmanteau of “block” and “charge” in Ames and you’ll instantly transport whoever hears it to one moment in 2000.

Iowa State entered the NCAA Tournament with a 29-4 record, 13 wins in their last 14 games, and Big 12 regular season and tournament championships. While many Cyclone fans thought they would earn a #1 seed, the Cyclones were instead slotted as the #2 seed in the Midwest Region, where #1 overall seed Michigan State awaited.

The Cyclones tore through their first three tournament games, winning each by double digits. This set up the Iowa State-Michigan State showdown that, to this day, some Cyclone fans believe was the real 2000 national championship game. Despite the 11-point final margin of victory, this was still the Spartans’ closest finish in the NCAA Tournament.

With 3:40 remaining and Iowa State holding a one-point lead, Marcus Fizer passed to Paul Shirley coming down the lane. As Shirley grabbed the pass, Spartan defender Charlie Bell slid in front of him. Shirley and Bell collided, sending Bell to the floor, as Shirley scored a layup.

Two officials blew their whistles and ran onto the floor. The official on the baseline signaled a charge against Shirley. The official on the sideline signaled a block against Bell. The outcome was a double foul, a block/charge, or a “blarge,” and it was one of many questionable calls that led to Iowa State head coach Larry Eustachy’s ejection from the game with 10 seconds to play and a five-point Michigan State lead. A total of 48 fouls were called in a game that led a young Skip Bayless to call the officials “nitwits” and “strictly amateurs.” Iowa State has yet to return to the Elite Eight since this game, and it is still the most recent Elite Eight game for any state of Iowa school.

2. #1 UNLV 84, #2 Iowa 81 – 1987 Elite Eight

The “blarge” is not the only time that an Iowa school has been close enough to the Final Four to taste it only to fall apart. In 1987, the Iowa Hawkeyes led the UNLV Runnin’ Rebels by 16 points at halftime in the Elite Eight. But Iowa, somehow, could not hold on to win the game.

It was a slow bleed for the Hawkeyes. After scoring 58 points in the first half, Iowa made only nine field goals in the last 20 minutes while shooting 36% from the floor.

With 16 seconds left, UNLV led 82-81 and Iowa had the ball. Kevin Gamble threw an alley-oop pass toward Brad Lohaus that could have given the Hawkeyes the lead. But Gamble’s pass was off the mark, striking the backboard and going out of bounds for a turnover.

It’s hard to imagine how fans would react to a game like this in the age of Twitter. A huge halftime lead in one of the biggest games in program history slowly disappearing because the team can’t score? It’s almost enough to reach #1 on this list. But the game that got the #1 spot is one that did happen in the Twitter era where an Iowa team gave away a big lead not over the course of one half, but over the course of one minute.

1. #3 Texas A&M 92, #11 Northern Iowa 88 (2OT) – 2016 Round of 32

If you’ve made it this far, you know that Iowa teams have had brutal heartbreakers for decades in the NCAA Tournament. But one game stands alone as one of the most improbable losses, not just for a state of Iowa team, but for any team in the history of March Madness.

Northern Iowa led by 12 points, 69-57, with 35 seconds left when Texas A&M came down with an offensive rebound. Northern Iowa still lost the game.

UNI turned the ball over three times in sixteen seconds to allow A&M to cut the deficit down to three. But the Panthers didn’t give up. A long pass led to two easy points that extended the lead to 71-66 with 18 seconds to play.

Texas A&M got an and-one with a score at the rim and made the free throw to get the score to 71-69. UNI inbounded the ball to guard Wes Washpun, who was stuck in the corner. With no timeouts, Washpun attempted to throw the ball out of bounds off of a Texas A&M player, but he missed. A&M grabbed the turnover and scored a quick bucket to tie the game at 71.

The game wasn’t over yet, as UNI still battled through two overtimes. But for those watching the game, it felt as though Texas A&M was destined to win as soon as the first overtime began.

Texas A&M’s rally from trailing by 12 points is the largest comeback in the last minute of a game in NCAA Tournament history, and the Aggies only needed about 35 seconds to do it. This all-time comeback at the hands of Northern Iowa seals the #1 spot on this list for the Panthers.

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While every Iowa school has has success–three have made a Final Four while Northern Iowa has made a Sweet 16–they have also experienced the pain that comes from being so close and coming up just short. As March Madness begins again this weekend, enjoy the thrilling games that result in pure joy for one team. Just know that for every incredible win, there is another team and another fanbase on the other end that will feel the heartbreak that Drake, Iowa, Iowa State, and Northern Iowa fans have known for years.

Honorable mentions (chronological): Iowa State’s loss to Utah in the 1944 Final Four, Drake’s loss to Kansas in the 1971 Elite Eight, Iowa’s loss to Louisville in the 1980 Final Four, Iowa State’s loss to UAB in the 2015 Round of 64, Northern Iowa’s loss to Louisville in the 2015 Round of 32.