Most realistic March Madness upset Kentucky can hope for in the South Region

“The tougher the journey, the sweeter the reward.” Well, it’s been over a decade since Kentucky basketball won a national championship, so I’m pretty sure that Big Blue Nation would take No. 9 however it came. If that means a top seed in the South Region slips up to make the path a little easier, then so be it. 

Now, the question is, which upset should Kentucky fans root for the hardest in the Round of 64? Obviously, Longwood knocking the No. 1 seed Houston out would be helpful, but there have only been two 16/1 upsets in the history of the NCAA Tournament and Kentucky would have to make it to the Elite Eight for that to matter. So, that may not be the upset to invest your emotional energy in during the first weekend. 

Upset that will clear the path to the Elite Eight for Kentucky

Instead, the upset that Kentucky fans should really root for is either Colorado or Boise State taking out Florida. I’m sure it won’t take much convincing for a bunch of Kentucky fans to root against an SEC rival, especially one that beat the Cats in Lexington in an OT thriller earlier this year. 

Whoever wins at the First Four in Dayton on Wednesday night will have a quick turnaround before facing Florida on Friday at 4:30 pm ET in Indianapolis. Yet, that team will have serious momentum after winning the No. 10 seed while Florida is reeling off a loss in the SEC Championship Game to Auburn, along with the loss of Mitch Handlogten to a season-ending leg injury. 

Despite that, Florida is still the biggest threat to keep Kentucky out of the Elite Eight. Marquette is the No. 2 seed in the region, but with the injury to All-American guard Tyler Kolek, the Golden Eagles are more vulnerable than ever. 

Florida, on the other hand, is a tough matchup for Kentucky, a team that can match the Wildcats offensively, but with bigger, more physical guards, and most importantly, more experienced guards. Zyon Pullin and Walter Clayton Jr. may not be the NBA prospects that Reed Sheppard and Rob Dillingham are, but their combined eight seasons of college basketball experience would likely pay off against the freshman duo. 

Kentucky matches up better against Marquette, giving Kolek nowhere to hide on defense. If Florida gets knocked out in the Round of 64, then Kentucky’s path to Elite Eight since 2019 is clear.