Bold Prediction: Kentucky Will Upset Ole Miss in Week Two

Kentucky Wildcats head coach Mark Stoops reacts after defeating the Mississippi Rebels at Vaught-Hemingway Stadium. Mandatory Credit: Petre Thomas-Imagn Images — Mark Stoops celebrates a win at Ole Miss, via Petre Thomas-Imagn Images

This time a year ago, I told you that Kentucky was going to upset Ole Miss in Oxford. If you listened to your Uncle Nick, you made money on the Wildcats’ only big win of the season. Uncle Nick is back to tell you that Kentucky is going to beat Ole Miss again, this time to snap an ugly 8-game home losing streak to Power Conference opponents.

Close Calls

Kentucky and Ole Miss couldn’t play more different styles. Mark Stoops relies on his defense and a physical rushing attack, while Lane Kiffin let’s it rip, regularly touting the most explosive offense in the SEC. For whatever reason, when those styles collide, it produces fireworks.

Mark Stoops has faced Ole Miss four times. The games have been decided by 10 total points, and the largest margin of victory is three. Kentucky only has one win in that stretch, but these two find a way to play close games.

Kentucky in SEC Home Openers

The week two loss to South Carolina was shocking for a myriad of reasons. One reason got overlooked at the time. Mark Stoops’ teams are typically at their best the first time an SEC team comes to Kroger Field.

Prior to the 31-6 shellacking by South Carolina, Kentucky was 5-2 in SEC home games in September, dating back to 2016. Why that’s the case cannot be succinctly explained, but it’s clearly a trend you cannot ignore.

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Ole Miss is in Rebuild Mode

Ole Miss went all in ahead of the 2024 season. With a three-year starter at quarterback and a slew of weapons at wide receiver, they went to the transfer portal to invest heavily in the trenches. It got em a few NFL Draft picks, but they ultimately fell short of the CFP, thanks in large part to the loss to Kentucky.

Pretty much every notable name from last year’s 9-3 team is gone after a record-breaking eight players were selected in the 2025 NFL Draft. Ole Miss ranks No. 113 in returning production. They are dead-last in the SEC, even behind a Kentucky team that has 50 new players on its roster.

Like the last two meetings against Kentucky, the Wildcats will be Ole Miss’ first true test of the season. It will be the first start for Austin Simmons against SEC competition and it’s away from the friendly confines of Vaught-Hemingway Stadium. Kentucky won in that venue in large part thanks to their play from the secondary, who prevented the Ole Miss wide receivers from creating explosives via yards after the catch. The only player the Wildcats are replacing in the secondary is Maxwell Hairston, who didn’t play in Oxford.

Nobody will expect Kentucky to do anything when the Wildcats and the Rebels are the featured SEC on ABC game of the week. That is why it will be even more satisfying when Mark Stoops drags Lane Kiffin’s team into the mud and delivers a much-needed feel-good win to Big Blue Nation.