Will Stein doesn’t need to say much about Alabama to understand what’s sitting in front of Kentucky this week.
The numbers do most of the talking. In 42 meetings since 1917, the Wildcats have beaten the Crimson Tide only twice.
Those victories came in 1922 and 1997, which means an upset of No. 13 Alabama on Saturday at Kroger Field would land with real historical weight.
It would also mean something bigger for a Kentucky program trying to claw its way back into national relevance.
That’s where the larger stakes come in for Stein. A win over Alabama would almost certainly hit hard on the recruiting trail, and that kind of momentum could accelerate what Kentucky is trying to build. The kind of turnaround the Wildcats want hasn’t been seen since Bear Bryant led them to the Orange, Sugar and Cotton Bowls in the 1949, 1950 and 1951 seasons.
Stein, though, is keeping his focus narrow.
Asked after Kentucky’s 45-13 win over Youngstown State on Saturday about facing one of the SEC’s most established powers, he brushed aside the noise.
“I don’t worry about it,” Stein said. “I just worry about my team, what we can control, making it about us.”
History says Kentucky has had a hard time doing much of anything against Alabama. The Wildcats are 2-39-1 all-time in the series, and they’ve only managed to stay within single digits five times in Alabama’s 39 wins. Since Kentucky’s 1997 upset, the Crimson Tide have won eight straight in the matchup by an average of 27 points.
That’s why the two UK wins over Alabama carry such a special place in the program’s story.
The first came on Nov. 18, 1922, on a rain-soaked day at Stoll Field, according to the Lexington Herald. In a scoreless third quarter, Kentucky quarterback Turner Gregg completed a 10-yard pass that set up halfback Bruce Fuller’s 6-yard touchdown run. Kentucky’s defense, which recorded five shutouts that season, then held off what one Lexington sportswriter called “the desperate aerial attack of the southern eleven” to preserve a 6-0 win.
The second came 75 years later and looked a lot different. Tim Couch connected with Craig Yeast on a 26-yard touchdown pass in overtime to lift Kentucky past No.
20 Alabama, 40-34, at what was then Commonwealth Stadium. It was Kentucky’s first overtime game ever, and after the “Couch to Yeast” finish, fans rushed the field and tore down the goal posts for the first time in the stadium’s history.
There was also a fitting twist to that 1997 night: Gregg, the winning quarterback from the 1922 game, was in the stands. At 97, he was invited into the Kentucky locker room after the game, where then-coach Hal Mumme handed him a game ball.
“Yeah, we gave (Gregg) the game ball, then he proceeded to chew Tim (Couch) out for not getting the team out of the huddle fast enough,” Mumme later recalled, laughing.
If Kentucky is going to pull off a third win over Alabama, there are at least a few details working in its favor.
Saturday will be Alabama’s first road game of 2026. In Kalen DeBoer’s first season in Tuscaloosa in 2024, the Tide dropped their first SEC road game, losing 40-35 at Vanderbilt. Last year, they lost their first road game overall, falling 31-17 at Florida State.
There’s also the quarterback angle. Alabama redshirt freshman Keelon Russell will be making his first road start as a collegian.
Kentucky got a taste of how much that can matter last season, when safety Ty Bryant picked off Ole Miss quarterback Austin Simmons twice in the first quarter of the SEC opener and helped the Wildcats jump out to a 10-0 lead. Ole Miss still came back to win 30-23, with Simmons finishing with 235 passing yards and 44 rushing yards.
Stein also made it clear Saturday that Kentucky wasn’t holding anything back against Youngstown State with Alabama in mind.
“We call the games to win,” Stein said. “... We’re not holding anything back.”
That matters because Stein’s own words from SEC Media Days are still hanging around. When he was asked why he believes Kentucky can finally become a winner under his watch, he said it was “because of me.”
So if Stein were to knock off Alabama in just his second game, it would do more than shock the league. It would give his early Kentucky tenure a loud, unmistakable edge - the kind of “called his shot” aura coaches dream about.
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Will Steins first game as Kentuckys head coach went about as well as the Wildcats could have hoped, with a season-opening win over Youngstown State giving the new staff a clean starting point. It also offered an early look at a roster that has talked plenty about its belief in the group, and the opener did enough to keep that optimism intact as Kentucky moved on to Alabama week.
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The catch for Alabama is that the film bank is thin, and what is available does not offer much of a clean blueprint. DeBoer said the Tide are leaning heavily on fundamentals as they get ready for an early conference test, which makes this more of a game-plan-for-the-basics week than a deep-dive into tendencies. The matchup is set for ABC and Disney+, and for Kentucky, that kind of uncertainty can be a useful place to be when a heavyweight comes to town. [Read more 🡒]