Wolff finished his collegiate basketball career at UConn after playing two years at LSU. He became the head coach at Boston University following the 1993-1994 season, taking over for Bob Brown. He was previously the head coach at Connecticut College, where he coached from 1980 to 1982. In between his head coaching jobs, Wolff was an assistant at St. Bonaventure, Wake Forest, SMU, and the University of Virginia. In his 13 seasons at BU, Wolff has 216-167 record, and Wolff has the most wins in school history. His career head coaching record is 246-185.
Dennis and his wife JoAnn have 3 children, Nicole, Matthew and Michael. Nicole played for the University of Connecticut women's basketball team, while Matthew is a redshirt senior on his father's team at Boston University.