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When was the last time Kentucky beat Alabama? Crimson Tide hold incredible series edge

With a new coach in Lexington, the Wildcats are hoping to turn the tide of history (pun very much intended).
ByEthan Lee
Sep 5, 2026; Lexington, Kentucky, USA; The Kentucky Wildcats take the field before the game against the Youngstown State Penguins at Kroger Field. Mandatory Credit: Arden Barnes-Imagn Images
Sep 5, 2026; Lexington, Kentucky, USA; The Kentucky Wildcats take the field before the game against the Youngstown State Penguins at Kroger Field. Mandatory Credit: Arden Barnes-Imagn Images | IMAGN IMAGES via Reuters Connect

While Week 1 went incredibly well for new head coach Will Stein and his Kentucky Wildcats, things are about to ramp up in difficulty for the first-year head coach. That's because he gets to face off against a program that the Wildcats essentially never beat, as Kentucky will take on the Alabama Crimson Tide on Staurday afternoon. And while plenty of programs struggle to beat Alabama historically, the Wildcats haven't come out on top against the Crimson Tide since 1997.

So, you know, it's been a few years. Nearly three decades, to be precise.

That means that this week, Stein is being tasked with something that [checks notes] Kentucky needed the combined brainpower and brilliance of Hal Mumme, Mike Leach and Tim Couch operating the Air Raid back in the system's early days to be able to pull off. And that was decades before Alabama decided that it'd be fun to have an offense of its own.

In that shocking 1997 win over the Crimson Tide at Commonwealth Stadium, the Wildcats needed overtime and 457 yards of offense to be able to get past what ended up being a pretty underwhelming Mike DuBose-coached Alabama team (they finished 4-7, which is a good reminder that there was indeed a time before Nick Saban when the Crimson Tide just weren't good).

But still, those in-game struggles for Kentucky? Well, that's largely due to the fact that the Cats had four turnovers in this game. Again, they still managed to move up and down the field against Alabama, generating 457 yards of offense in this game. Oh yeah, and they won 40-34.

Before 1997, when was the last time Kentucky beat Alabama?

Tim Couch
Tim Couch | Andy Lyons/GettyImages

Let's go back a little bit further and take a look at some more history between these two programs. Because even though they don't play all that often anymore, they used to play pretty regularly — and it's worth keeping in mind that this series is among the most lopsided in all of college football.

Alabama has an overall series lead of 39-2-1 over Kentucky. There's that really intriguing 1997 win for the Wildcats that involved overtime, a blocked kick and the tearing down of goalposts postgame. And then there's a win all the way back in 1922.

And that is it — just those two wins for the Wildcats. So Stein and his offense are being asked to find a way to do something that is functionally unprecedented for this Kentucky football program. Alabama has won eight consecutive games in this series and had won the 14 meetings prior to that loss in 1997.

Interestingly enough, the 1997 win for Kentucky had an identical margin of victory as the 1922 win did: six points. They were wildly different games; back in 1922, the Wildcats won 6-0 over Alabama. A game featuring a total of six combined points between the two teams is a bit different than one involving 74 combined points and close to 900 yards of offense.

So, will Stein and Kentucky find a way to get the Wildcats a win that would increase their win total against Alabama by a full 50 percent? It doesn't seem all that likely.

Again, Kentucky just typically doesn't win these games all that often. Still, ESPN's Matchup Predictor is giving the Wildcats a 15.4 percent chance of coming out on top (and miracles certainly can happen).

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