ESPN picks the winner between Kentucky and Ole Miss

Can Kentucky pull off the home upset against the Ole Miss Rebels?

Sep 28, 2024; Oxford, Mississippi, USA; Mississippi Rebels head coach Lane Kiffin (left) and Kentucky Wildcats head coach Mark Stoops (right) shake hands after the game at Vaught-Hemingway Stadium. Mandatory Credit: Petre Thomas-Imagn Images | Petre Thomas-Imagn Images

Mark Stoops and the Kentucky Wildcats got their season started on Saturday against the Toledo Rockets, where the Wildcats were able to pick up the 24-16 win. Now things are set to get a lot harder for the Wildcats as Lane Kiffin and the Ole Miss Rebels are coming into town.

Last week, Ole Miss got their season started with a 63-7 win over the Georgia State Panthers, where their quarterback Austin Simmons threw for 341 yards and three touchdowns. Simmons also did have two picks in this win.

Aug 30, 2025; Oxford, Mississippi, USA; Mississippi Rebels quarterback Austin Simmons (13) drops back to pass during the first quarter against the Georgia State Panthers at Vaught-Hemingway Stadium. Mandatory Credit: Petre Thomas-Imagn Images | Petre Thomas-Imagn Images

While Simmons did get some playing time last season, this start at Kentucky is going to be his first big-time road start, so Big Blue Nation needs to get Kroger Field rocking to make things tough on Simmons.

In Kentucky's first game of the season against Toledo, Zach Calzada didn't have a great showing. He was 10-23 for 85 yards and an interception with no touchdowns through the air. Calzada did score with his legs, but this team did not get much going through the air.

While Calzada didn't have the best debut at Kentucky, he has proven during his long college football career that he is more than capable of winning big football games, and he will have another opportunity on Saturday.

Kentucky’s quarterback Zach Calzada (5) with a complete pass against Toledo Saturday afternoon at Kroger Field. August 30, 2025 | Scott Utterback/Courier Journal / USA TODAY NETWORK via Imagn Images

While Kentucky has had its fair share of struggles of late, they have given Ole Miss fits, especially last season when Stoops and company went into Oxford and took down the Rebels.

ESPN doesn't seem to be confident in the Wildcats' chances in this game, as they only give Kentucky a 16.4% chance to get the win. The spread on Monday sits at -9.5 in favor of the Rebels.

If Kentucky is going to find a way to win this game, Calzada will have to get things going through the air. He was overthrowing just about every deep ball on Saturday, and the Wildcats will need some explosive plays to win this football game.

This game is set to kick off at 3:30 on Saturday, and hopefully Kroger Field will have a ton of energy as the Wildcats look to upset Ole Miss once again.