He first played in the NHL for the Montreal Canadiens during the 1968–69 season. He was only the third American college player selected by an NHL team. Esposito made his NHL debut against the Oakland Seals, playing 26 minutes in relief of Rogie Vachon. His first NHL start was against the Boston Bruins, then led by his brother Phil. The game ended in a 2–2 tie, in which Phil scored both goals for Boston and Tony made 33 saves. Esposito played thirteen regular season games, due to both Gump Worsley and Vachon being injured. However, Esposito returned to the minors when they both returned from their injuries. Worsley was injured again during the playoffs, so Esposito was called again. Tony Esposito served as backup to Vachon, dressing for all four games in the finals. As the Canadiens club was deep in goaltenders at that time, with Worsley, Vachon and other prospects in the system, Esposito was left unprotected by the Canadiens in 1969.