After college, Driesell served three years in the United States Navy and attained the rank of lieutenant. He coached the Naval Academy Preparatory School from 1985 to 1988 and compiled a 40–29 record. In 1989, he joined his father, Lefty, as the associate head coach at. He coached there until 1994, and during that time, the Dukes won five consecutive outright or shared Colonial Athletic Association regular-season championships, which was a NCAA record at the time. James Madison participated in the 1994 NCAA tournament, where they were eliminated in the first round by third-seeded Florida, an eventual semifinalist team. From 1997 to 2003, Driesell was the head coach at Marymount University, a Division III school in Arlington, Virginia. In 1999, he also assumed the role of assistant athletic director. During his six-year tenure as head coach, the Saints compiled an 88–72 record, and secured the 2000 Capital Athletic Conference tournament championship and the team's first-ever bid to the NCAA Division III tournament. During the 2003–04 season, he worked at Georgetown as the Hoyas' recruiting coordinator and an assistant coach. From 2004 to 2006, he was the head coach of the Bishop Ireton High School basketball team. In 2006, Driesell was hired by Gary Williams as an assistant coach at the University of Maryland, the alma mater of both men. Williams said Driesell was hired strictly on his merits, and said, "Chuck was hired based on what he was as a basketball coach. Naturally genes don't hurt, but I wouldn't hire someone just because he is someone's son if I didn't think he was a very good basketball coach." Driesell replaced Rob Moxley who left for a position at the UNC Charlotte. Driesell served as Maryland's lead recruiting coordinator and was the assistant coach responsible for "advance scouting, player development, and game preparation." On April 28, 2010, Driesell was hired as head coach of The Citadel. He replaced Ed Conroy, who had left for Tulane. Since being at The Citadel, Driesell has won only 27.1 percent of his games. With four players returning who had started since their freshman years, Driesell only won ten games. The lowest number of wins for those players since they were freshman. On March 10, 2015, The Citadel announced that it would not renew Drisell's contract. On April 22, 2015, San Jose State head coach Dave Wojcik added Driesell to his staff as an assistant coach. Wojcik had been an assistant coach at James Madison under Lefty Driesell. However, on June 5 Driesell was named as head coach of the Maret School in Washington, D.C. In his second year at Maret, he led the team to a MAC Co-Championship, as well as the DCSAA finals, where they lost to Gonzaga College High School 77-66.
