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Predicting a Kentucky Football upset that would skyrocket Will Stein's first season

One big-ticket upset win could change the trajectory for Will Stein's first season at Kentucky in the best way.
Dec 3, 2025; Lexington, KY, USA; Kentucky Wildcats head football coach Will Stein speaks during his introductory press conference at Nutter Field House. Mandatory Credit: Jordan Prather-Imagn Images
Dec 3, 2025; Lexington, KY, USA; Kentucky Wildcats head football coach Will Stein speaks during his introductory press conference at Nutter Field House. Mandatory Credit: Jordan Prather-Imagn Images | IMAGN IMAGES via Reuters Connect

Will Stein has folks excited for the future of Kentucky Football once more, and that alone sets him apart from the waning years of the Mark Stoops era. Big Blue Nation is as involved as era on the recruiting trail and online as Stein builds a 2027-28 class worthy of national attention. But before that, we should be careful not to overlook the team at hand.

The current Cats are widely projected around the 4.5 win mark in what is generally seen as a reset year. But what if, at the season's most crucial turning point, Stein and his crew of underdogs (undercats?) upset the biggest personality in the sport?

Lane Kiffin and his own first-year football team, the LSU Tigers, come to Kroger Field in week six. For whatever reason, Kentucky Football has a history of causing very good Kiffin-coached units a lot of trouble.

Mandatory Credit: Matthew Hinton-Imagn Images
Dec 1, 2025; Baton Rouge, LA, USA; LSU new head coach Lane Kiffin speaks at South Stadium Club at Tiger Stadium. Mandatory Credit: Matthew Hinton-Imagn Images | IMAGN IMAGES via Reuters Connect

Two seasons ago, an underwhelming Wildcats team marched onto Ole Miss' home field and upset the No. 14 Rebels in a real shocker. Then, in Stoops' last go, the No. 20 Rebels squeaked away from the Cats in Lexington by just one touchdown.

With a new coach in the driver's seat and Kiffin returning to the Bluegrass for the second straight season, I think it's time Kentucky gets another one over on the guy.

A Big Win at the Perfect Time

After opening the 2026-27 season at home against Youngstown State, Kentucky will face SEC powerhouses Alabama (home) and Texas A&M (road) in back-to-back weeks. Then, it's a hopeful pitstop against South Alabama before traveling to South Carolina for another conference brawl.

At either 3-2 or 2-3, assuming a big upset doesn't come earlier, a victory over LSU at this juncture could define Kentucky's season. It'll be the second time that Kroger Field gets to host a SEC opponent at that point, and the first to take place at night.

The stadium is gonna be on fire, especially with all the hype surrounding Stein's first run. This is where the Cats head coach draws a line between the previous regime and his own, and he'll most likely do it by way of an all-out offensive raid.

Beating Kiffin at His Own Game

I can't drum up a better response to the struggles of the Stoops era than to get an early signature win in exactly the opposite fashion to recent blue and white teams.

Led by quarterback Kenny Minchey who, by all accounts, can absolutely sling it, Will Stein's nation-leading offensive tendencies would have to fully come out for Kentucky to outpace what is likely to be a similar approach from Kiffin.

When Kentucky competes with Kiffin, it's most often the result of a defense-first, gritty approach. I believe this one, on the other hand, has the looks of a full-on shootout. It's impossible to tell exactly how this Cats team will look on the field, but what we've seen already suggests a group capable of more than four wins.

But the nature of Kentucky's gauntlet schedule assumes an unexpected win to slide in somewhere. Maybe it's wishful thinking, but I'm penciling the October 10 date with the Tigers as that very win. You have to stand for something, BBN, or you'll fall for anything.

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