He played for the St. Bonaventure Bonnies from 1996 to 2000 and was named to the Atlantic 10 All-Conference first team in his senior year.

Winn played for La Salle Senior High School in Niagara Falls.

[4][5][6] In Winn's senior season, 1999–2000, he averaged 13.6 points per game and led the Bonnies in scoring.

[5] After college, Winn played professional basketball in several leagues in the United States and overseas.

[7] Winn lives in Charlotte, North Carolina, with his wife, Tamaron and 2 sons Tim Jr and Rhasheen.