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Heartbreak ‘Hoos: Ranking the most gut-wrenching losses in March Madness

It’s never easy, but the Furman loss can remind us about some similar outings in March that resonate today.

<p>Virginia's 2018 loss to UMBC marked the first loss by a No. 1 seed to a No. 16 seed in March Madness history.</p>

Virginia's 2018 loss to UMBC marked the first loss by a No. 1 seed to a No. 16 seed in March Madness history.

As Virginia sports fans at large, we’re incredibly spoiled. Not many schools can boast 32 national championships — including one in a major-market sport that gave us some much-needed argument points against the Dukes and North Carolinas of the world. I think I was just so relieved that I didn’t have to use the “But we have more regular-season titles in the last six years!” speech that I mastered. Virginia’s basketball highs—national  may outweigh the lows after the 2019 National Championship, but we’ve seen our fair share of heartbreak. Some hurt more than others, though, so here are my five most upsetting March Madness losses.

1. No. 1 Virginia vs. No. 10 Syracuse, Elite Eight, 2016

The top-seeded Cavaliers looked poised to coast to their third Final Four in program history, having handled the likes of Iowa State and Butler before matching up with an ACC foe in the Elite Eight. Surprisingly enough, and harder to digest, Syracuse snuck into the tournament as a 10 seed and held a 19-13 record. Virginia, on the other hand, finished the season fourth in the AP Poll and second in the ACC. 

The Cavaliers were up by as much as 15 in the second half against the Orange and carried a 14-point lead into halftime. Before this fateful Elite Eight outing, Coach Tony Bennett’s teams were 68-0 when leading by double-digits at the break. Thanks to the heroics of Syracuse guard Malachi Richardson, though, the record failed to stay perfect.

The 15-point lead still keeps me up at night. An offensively-dominant Virginia team — complemented by the nation’s second-leading scoring defense — couldn’t waltz into the Final Four with a massive lead in the last ten minutes? Well, Richardson’s 21 second-half points didn’t help the Cavaliers’ case.  I will never forgive Syracuse for what they did, yet perhaps Virginia’s current five-game win streak over the Orange counts as revenge.

2. No. 1 Virginia vs. No. 16 UMBC, Round of 64, 2018

All I could feel was shock as I slowly realized that we would be the first one seed to fall to a 16. This was a Virginia team that raced through the ACC with a 31-2 record, slayed Duke after a dagger three-pointer from then-sophomore Ty Jerome and looked poised to avenge some prior tournament losses. Even if no one predicted the Cavaliers to attain that No. 1 overall seed in March — having gone unranked in the preseason AP Poll — expectations were higher than ever after Virginia knocked off No. 12 North Carolina in the ACC Championship. 

Nonetheless, we had to swallow the fact that Virginia would lose in a big way to the small school in Baltimore, Md.  before the game even hit the 9:33 mark in the second half.

I remember ditching the living room to distract myself by watching Netflix upstairs, waiting for my dad to come upstairs to tell me that we had made a Syracuse-like run. Like so many others, I tried to escape reality with UMBC. 

I’ve come to terms with this one better than Syracuse on account of the Retrievers’ ludicrous three-point percentage — 50 percent on 24 attempts — which basically means very, very few teams were beating them that night. However, this one still stings.

3. No. 4 Virginia vs. No. 13 Furman, Round of 64, 2023

This is the loss that prompted me to write this piece. I’m sure that many other Cavalier fans didn’t think that we could possibly drop two-straight tournament games to a 13 seed — thanks to Ohio the year before — yet reality hit us in the face once again. A loss would have meant three first-round exits in the last four tournament appearances, a horrible stain for a program that had reached the pinnacle of college basketball. Furman didn’t even shoot the ball like UMBC, even if they made 10 threes to our two, and their top scorer fouled out in the last 10 minutes of the second half.

Moreover, the Cavaliers spoiled yet another big lead in the second half — having gone up by as much as 50-38 in the second half after a three-pointer from freshman Isaac McKneely. Naturally, the Paladins crawled back into the game yet looked to be staring defeat in the face, until The Pass. 

Graduate student guard Kihei Clark will forever be remembered for his two passes — one which sent Virginia to the Final Four in 2019, and the other which occurred just before the clock wound down against Furman. Clark’s blunder against the Paladins following a double-team on the baseline will not be forgotten any time soon. However, he is still a legend in Charlottesville, a feisty defender and consummate point guard who should be revered for his dedication to this program.

The last 20 seconds of this game, however, just about made me lose my mind. A two-point lead suddenly evaporated after a three-pointer from Furman guard JP Pegues — who had missed his last 15 three-point attempts — caught nothing but net.

There’s a lot to digest in this one. 

4. No. 1 Virginia vs. No. 4 Michigan State, Sweet 16, 2014

Michigan State was a four seed playing in one of the toughest conferences in basketball — the Big Ten — yet Virginia just had that “it” factor in 2013-14. This was a team that throttled No. 4 Syracuse by 19, beat No. 7 Duke in the ACC Championship and looked the part of the next Virginia Final Four team. When reflecting on the 61-59 loss to the Spartans at Madison Square Garden, the personnel Bennett possessed makes the “what could’ve been” case that much more haunting.

A backcourt of two future NBA players — Malcolm Brogdon and Joe Harris — aligned perfectly with a well-rounded frontcourt of Mike Tobey and Akil Mitchell, while Virginia fan favorite London Perrantes showed remarkable poise as a starting freshman point guard. In addition, future ACC Defensive Player of the Year — Darion Atkins — came off of the bench, alongside athletic phenom Justin Anderson and another current NBAer in Anthony Gill. Depth was not a problem for this team — one of my favorites of the Bennett era.

The nail-biting aspect of the Michigan State game — combined with the talent that year — makes it an easy call here at No. 4. It’s just unfortunate that Virginia had to play one of the best four seeds known to man.

5. No. 2 Virginia vs. No. 7 Michigan State, Round of 32, 2015 

The Spartans were public enemy No. 1 in 2014 and 2015. What luck for Virginia that they had to face off with — once again — an underseeded Tom Izzo team that made the Elite Eight a year prior. This was another Bennett team with such incredible potential, having only lost four games and having returned the bulk of their starpower. Also, a kid with Malachi Richardson-type energy put the nail in the coffin in the Round of 32.

Travis Trice couldn’t miss against the Cavaliers. This guy was the first example of “Man, he’s incredibly annoying” that we saw with Richardson and Purdue’s Carsen Edwards later on. A 23-point effort and a four of eight three-point clip — doubling Virginia’s number of three-point makes as a team — was the nail in the coffin for an offensively challenged Cavaliers squad.

Virginia doubled down on disappointment against Michigan State, advancing no farther than the Sweet 16 after finishing with a combined 60-11 record over two years. Thanks, Sparty.  

Nonetheless, I still love you, Virginia basketball. 

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