He played junior hockey for the Verdun Juniors and the Verdun Junior Canadiens from 1983 to 1986. Undrafted by any NHL club, Fleming went on to the University of Prince Edward Island from 1986 to 1991. During that time he also played senior hockey for the Fredericton Alpines and the Charlottetown Islanders. In 1991 he signed as a free agent with the Montreal Canadiens. He played almost exclusively with the Fredericton Canadiens until his retirement in 1998. He did get a five game callup to Montreal in 1993-94 and six games in 1994-95, scoring no points.