Kentucky has been a college basketball powerhouse under longtime coach John Calipari, but it only has one national championship in 2012 to show for it.
The rest of Calipari’s time as coach of the Wildcats is filled with March Madness disappointments, as the school has endured some heartbreaking losses over the years. It’s also taken some absolutely baffling defeats in March, particularly considering the quality of players that Kentucky typically recruits to play in Lexington.
Plenty of talented Kentucky teams have failed over the years to get as far as expected in March Madness, but these five losses feel like the worst ones taken in Calipari’s time. There are some that may hurt Kentucky fans more (particularly those in the Final Four and Elite Eight), but these five games don’t make a ton of sense for why they registered as Kentucky losses.
They’re bad in the questionable way, and we apologize to Wildcats fans if they bring back some tough memories.
5. 2018 men's NCAA tournament Sweet 16 loss to Kansas State
A Kentucky team with led by 2024 NBA MVP contender Shai Gilgeous-Alexander and NBA players like P.J. Washington and Nicholas Richards couldn’t overcome a ninth-seeded Kansas State in the Sweet 16 despite holding a five seed in 2018.
It was a tough loss for a Kentucky team that had the talent to go much further than this but got taken out by a K-State team with one NBA player (Dean Wade). Not to mention, that Wildcats team was later eliminated in the Elite Eight by 11 seed Loyola-Chicago in that school’s historic run.
4. 2013 NIT first-round loss to Robert Morris
The year after Kentucky won the only national championship of Calipari’s tenure with the school, it failed to make the NCAA tournament and somehow lost as a one seed in the NIT to eight seed Robert Morris. That Wildcats team didn’t have future NBA player Nerlens Noel for this game, but it did have guys like Willie Cauley-Stein, Alex Poythress, Archie Goodwin, Ryan Harrow and Jarrod Polson. You’d have thought that group could win an NIT game, at least.
3. 2019 men's NCAA tournament Elite Eight loss to Auburn
After beating the Auburn Tigers twice in the regular season, a two seed Kentucky couldn’t keep that momentum going in the Elite Eight and lost to a five seed Tigers team. Returning Wildcats players like Washington and Richards were joined by future NBA standouts like Tyler Herro, Keldon Johnson, Immanuel Quickley and Ashton Hagans.
Losing to an SEC seed lower than you after defeating them twice in the regular season with that Kentucky roster in particular had to hurt. It’s really confusing how they dropped this one.
2. 2024 men's NCAA tournament first-round loss to Oakland
Thursday’s loss to the 14 seed Oakland felt like a new low for the Wildcats, but it wasn’t quite the worst loss in the tournament of the Calipari era. However, it was pretty awful and might cost the longtime coach his job.
1. 2022 men's NCAA tournament first-round loss to St. Peter's
The worst loss of Calipari’s time as the coach of Kentucky came in 2021, when the two seed Wildcats were absolutely stunned by 15 seed St. Peter’s in the first round. That Wildcats team boasted future NBA talents like TyTy Washington, Jacob Toppin and Oscar Tshiebwe, but it still lost to a 15 seed in the first round.
That was absolutely brutal for the Wildcats and might’ve been the beginning of the end for this era of Kentucky basketball.
