Cunningham attended Headland High School in Alabama. He struck out 77 batters as a senior across 46 innings of work, while sporting a 0.76 ERA, and was named to the 2021 All-Alabama State First Team. He was ranked the 4th best right handed pitcher in the state and the 9th best prospect overall. He chose to join Vanderbilt following his high school career.
As a freshman, Cunningham made 12 appearances including 6 starts. He held a 4.59 ERA through 33.1 innings pitched. He struck out 27 batters and walked 14.
Last season as a sophomore, Cunningham pitched mostly out of the bullpen, making 18 appearances and just 4 starts. He struggled a bit, having a 6.43 ERA in 42 innings pitched. He struck out 45 batters and walked 23.
This season as a junior, Cunningham has taken over a starting rotation spot, and is expected to take a step forward, recovering from last year's struggles.