Coming out of high school, Cupp was rated as a five star recruit where he held offers from schools such as Alabama, Florida, Georgia, LSU, Notre Dame, Ole Miss, Texas and Texas A&M.
[2] Ultimately, Cupp decided to commit to play college football for the Texas A&M Aggies.
[7] After the conclusion of the 2021 season, Cupp decided to enter his name into the NCAA transfer portal.
[10][11] In Cupp's two seasons at Texas Tech in 2022 and 2023 he played in 24 games, totaling 23 receptions for 246 yards and four touchdowns.
[12][13] Cupp was signed by the Kansas City Chiefs as an undrafted free agent after the 2024 NFL draft.