[2][3] Chuck attended the University of Maryland, and played on the basketball team coached by his father as a shooting guard from 1981 to 1985.
Driesell participated in four postseason tournaments (one NIT and three NCAA) and was also a member of the 1984 Atlantic Coast Conference (ACC) championship team.
James Madison participated in the 1994 NCAA tournament, where they were eliminated in the first round by third-seeded Florida, an eventual semifinalist team.
[4] From 1997 to 2003, Driesell was the head coach at Marymount University, a Division III school in Arlington, Virginia.
[4] In 2006, Driesell was hired by Gary Williams as an assistant coach at the University of Maryland, the alma mater of both men.
[5] Driesell served as Maryland's lead recruiting coordinator and was the assistant coach responsible for "advance scouting, player development, and game preparation.
However, on June 5 Driesell was named as head coach of the Maret School in Washington, D.C.[11] In his second year at Maret, he led the team to a MAC (Mid-Atlantic Athletic Conference) Co-Championship, as well as the DCSAA (District of Columbia State Athletic Association) finals, where they lost to Gonzaga College High School 77–66.