He was a five-star recruit who previously played professionally for the Cold Hearts and Blue Checks with Karter Knox in Overtime Elite during what would have been his senior year in high school.

[6] As a sophomore, he averaged 21.2 points, 4.9 assists, 4.1 rebounds and 2.1 steals per game, leading his team to a 29–3 record and a non-association state title.

[8] On December 1, 2021, he committed to playing college basketball for NC State over offers from Memphis, LSU, Kansas and Kentucky.

[1] Sources: On November 3, 2022, Dillingham left Donda Academy after multiple controversies surrounding its founder, Kanye West, and signed with Overtime Elite, a professional basketball league for late-high-school- and early-college-level players.

[12] Dillingham made his OTE debut for the Cold Hearts on November 11, recording six points, three rebounds and three steals in a 92–84 loss to the YNG Dreamerz.

[12][13] After spending one season with the University of Kentucky, Dillingham declared his entry into the 2024 NBA draft and received a green room invite.