In July 2020, Diggins, the No. 41 recruit in the country and a 4-star recruit, announced his commitment to the University of Connecticut.[2] He received 21 Division I offers coming out of high school.
Diggins began his college basketball career with the UConn Huskies in 2021. As a freshman with the Huskies, Diggins appeared in 9 games and averaged 0.8 points per game.[3]
Diggins transferred to the UMass Minutemen for his sophomore season.[4] As a sophomore, he appeared in 26 games and averaged 4.7 points per game.
As a junior with UMass, Diggins had a breakout season, starting in all 31 games for the Minutemen and averaging a career-high 12.8 points per game, 2.4 rebounds per game, and career-highs in FG% and 3P%. After his junior season he was named the 2023-24 Atlantic-10 Conference Most Improved Player.
As a senior, Diggins started all 32 games he appeared in and averaged a career-high 16.8 points per game at UMass. He was named to the 2024-25 All-A-10 team.[5] On January 15, 2025, in a game against the Fordham Rams, Diggins set the UMass program single-game scoring record with 46 points in a 3OT win.[6]
Professional career
On November 6, 2025, Diggins was named to the Maine Celtics opening night roster.[7]
On November 12, 2025, Diggins made his NBA G League debut against the Raptors 905, appearing for 14 minutes and scoring 4 points.[8]