We’ve talked about it in great detail over the last few months. Ever since Will Stein was hired as Kentucky’s new coach, there’s been a buzz around the program that hasn’t been there for a few years. Need evidence of that? All you have to do is watch his speech at SEC Media Days. Stein drew a lot of attention to not only himself but the program with a couple of his quotes. Most notably when he said Kentucky would be successful because of him. Nothing like some confidence to be sure. However, now the Wildcats have to back it up on the field. Unfortunately, the SEC schedule makers did the Wildcats no favors. By one measure, Kentucky has the fourth toughest schedule in the country. Even so, there’s a path to a bowl game. Today, we’ll outline how they get there with Must-Win Games for Kentucky in 2026.
Must-Win Games for Kentucky in 2026
For the purposes of our writing today, we’ll assume the Wildcats beat Youngstown State in the season opener and South Alabama on September 26th. That puts the Cats 1/3 of the way to six wins and a bowl game. However, to get there, Stein’s club needs to get back on the right side of some rivalries.
Tough Road Test
October 3rd- At South Carolina- Let’s be honest, we’re going to miss the passive-aggressive back and forth between former UK coach Mark Stoops and Gamecock head man Shane Beamer. From 2000-2013 Carolina won 13 of 14 meetings. Then from 2014-2021 the Wildcats flipped the script, taking seven of eight. Unfortunately for the Big Blue Nation, it’s gone back towards the Gamecocks as they’ve won the last four. Of course, playing in Columbia we’ll be treated(?) to “Sandstorm” approximately a billion times.
Getting Back On Track
October 24th- Vanderbilt- Diego Pavia is gone from down in Nashville, and folks around the SEC are wondering if the Commodores can maintain their recent success without him. Five-star quarterback Jared Curtis, the highest-rated recruit in school history, takes over. Clark Lea got him to flip from Georgia. Kentucky won six straight from 2016-2021. However, Vanderbilt has won three of the last four and the last two in Lexington.
Continuing our look at must-win games for Kentucky in 2026, let’s move to a rivalry that’s been on the Wildcats’ side recently.
Keeping The Streak Going
November 14th– Florida– The Gators have a new coach who’s very familiar to Wildcat fans, in Jon Sumrall. A scheduling quirk sends Florida back to Lexington for a second straight year. We all know about the 31-game win streak the Gators had over the Wildcats. However, Kentucky’s won four of the last five and should make it five of six.
Columbia Times Two
November 21st- At Missouri- These former SEC East rivals met every year from 2012 to 2023 when the Tigers joined the league. However, when the SEC went to 16 teams, they haven’t played the last two years. Overall, Kentucky leads the series 8-5, but the Tigers won the last meeting back in 2023. Winning at Faurot Field is always tough, and it’s a second SEC trip to Columbia that will be a major test.
Let’s wrap up Must-Win Games for Kentucky in 2026 by looking at the huge in-state rivalry.
Taking Back The State
November 28th Louisville– Another rivalry that the Cats had dominated, which recently flipped. Between 2016 and 2023, UK won six of seven contests. The two schools didn’t play in 2020’s COVID year. Since taking the job in Louisville, Jeff Brohm’s Cardinals have dominated the Wildcats 82-14 over the last two years. You want to get the Big Blue Nation behind you in a hurry? Beating Louisville and taking back the Governor’s Cup is a great start.
Final Thoughts
As we mentioned in the beginning, Stein said all the right things during “Talking Season.” In addition he’s believes they’ve got a potential star in the making in quarterback Kenny Minchey. Furthermore, the Big Blue Wall looks to be rebuilt to the days when John Schlarman led the line.
However, in his first season, they’ve got to find a way to win. We’ve outlined five games that could go either way for the Cats in 2026. Win all five, and they are looking at a pretty good bowl game. Take four of the five and UK’s still going bowling for the first time since 2023. Anything less than that and the Cats must pull at least one upset from one of the nation’s toughest schedules to get back to the postseason.
Most national pundits don’t think Kentucky will win more than five games. Our first bowl projections don’t feature the Wildcats either. However, we’re only in July, and there’s an entire season left to play. Can the Wildcats do it? We shall soon see.
Thanks for checking Must Win Games For Kentucky In 2026 here at Last Word On College Football. Next time, we’ll start going position by position through Stein’s first squad.
Main Image: Nathan Ray Seebeck-Imagn Images
