Kentucky enters year one of the Will Stein era, as he replaces the previously longest tenured coach in the league Mark Stoops.
The schedule is brutal for the Wildcats. They’ll face three playoff teams from a season ago, and nine of their ten games against Power Four teams are projected to finish .500 or better. Stein doesn’t have to deliver a huge first season, but winning a few defining games while building an exciting, entertaining brand of football would be a major step in the right direction.
Strength of Schedule: 3rd in the SEC
It’s not going to be easy for Will Stein in year one. Kentucky, once again, will play the first SEC game of the year. Last year, it was Ole Miss. This season, Alabama comes to town before a road trip to Texas A&M. October brings a three-game stretch against South Carolina, LSU and Oklahoma, with two of those matchups on the road. Then, in November, they face former SEC East rivals Tennessee and Florida in back-to-back weeks.
It’s the third hardest schedule in the SEC as we illustrated in our previous look at the toughest schedules in the SEC.
Biggest Game of the Year: Louisville
It’s a rivalry game, so obviously. The bigger picture part of this, though, is the ceiling being very low in year one for Will Stein while still having the opportunity to end the season on a high note.
Kentucky controlled this series for much of the late 2010s and early 2020s, winning six of seven meetings from 2016 to 2023. That dominance came to an abrupt end over the last two seasons, as the Wildcats surrendered 41 points in each game and were outscored 82-14.
Louisville and Kentucky are very similar in that they are both basketball schools who have recently still found a way to pledge a great deal of resources to football. With the hiring of a new coach, Kentucky committed a lot to NIL and Will Stein to win and win right away.
He doesn’t need to make the CFP anytime soon, but beating a team that’s projected at eight wins in year one would be massive to keep the fanbase invested.
Best Chance at an Upset: Florida
Florida will travel to Lexington in mid-November to play in a series they have absolutely dominated historically. The Gators could be vulnerable here, though. They’ll be coming off back-to-back games against Georgia and Oklahoma, and could very well be limping towards the finish line under a first year head coach.
Kentucky’s roster isn’t devoid of talent. That game can be closer than most think, and the Wildcats play pretty well at home in November. In fact, last year’s game ended in a 38-7 rout of Florida.
Toughest Stretch: Week 5 through 7
There’s no real easy part of the schedule for the Wildcats in 2026. The schedule starts with two former CFP teams (Alabama and Texas A&M) in Week 2 and 3 in early September. They play ten Power Four opponents, and nine of them are projected to win at least six games according to various sportsbooks.
The month of October, however, is the worst of the worst when it comes to schedule difficulty. Kentucky will go to South Carolina, return home to face LSU, and then go back on the road to play Oklahoma. They will be favored in just two of their first seven games, and that stretch is almost assuredly going to result in an 0-3 record.
If they start 2-5 it wouldn’t be the craziest or most unexpected thing that could happen. It would, however, divert a majority of the fanbase’s attention to basketball season, and that is not ideal for a first year head coach.
Biggest Trap Game: Vanderbilt
On the heels of the aforementioned brutal three game stretch to start October, Kentucky will close out the month with a home game against Vanderbilt.
The Wildcats have lost three of their last four games to Vanderbilt, including last year’s 28 point defeat. Kentucky could be favored in this one considering the amount of production that Vanderbilt has to replace from last year’s ten win team.
The ‘Dores will be starting a true freshman quarterback, and the last thing Kentucky needs is to lose at home to a freshman quarterback in a rebuilding year for the historically worst team in the league.
Ceiling and Floor: 7-5 and 3-9
There are few teams in the country that are a bigger mystery this season than Kentucky. It’s hard not to love what they did in the portal adding 29 players with 20 coming from Power Four schools and 14 from the SEC.
There are multiple former five-star recruits and former elite portal stars that just never seemed to pan out at previous starts. Kenny Minchey is going to succeed in this offense, but it might not be enough to win more than six or seven games in year one because of the difficulty of the schedule.
Full disclosure, I hate the prediction I’m making because I do believe in the roster and newfound resurgent energy in the program since Stein took over. I’m not sure I believe in the defense at all though, and that’s a big problem if you want to succeed in this league.
Season Prediction: 4-8
Youngstown State – W 45-14
Alabama – L 21-31
At Texas A&M – L 17-30
South Alabama – W 38-20
At South Carolina – L 23-34
LSU – L 24-38
At Oklahoma – L 13-28
Vanderbilt – W 27-20
At Tennessee – L 23-28
Florida – L 17-27
At Missouri – L 27-28
Louisville – W 33-30
Previous Schedule Predictions and Breakdowns
