Cunningham attended Park Crossing High School in Montgomery, Alabama.
[3][4] After redshirting his first year at Louisville in 2017, Cunningham appeared in 10 games and made three starts in 2018.
Following the conclusion of the 2023 NFL draft, the New England Patriots signed Cunningham as an undrafted free agent.
[11][12] On October 14, 2023, the Patriots promoted Cunningham to the active roster on a three-year contract.
[15][16] The Baltimore Ravens signed Cunningham off the Patriots' practice squad on December 12, 2023.