Tremblay was hired four games into the 1995–96 season as head coach of the Canadiens although he had no previous coaching experience. As coach, he developed a long running dispute with star goaltender Patrick Roy, which eventually led to Roy's departure from Montreal. The two had almost come to blows in a Long Island coffee shop before Tremblay was announced as coach, and Roy snickered when Tremblay arrived in the dressing room for the first time. They almost fought a second time after Tremblay fired a shot at Roy's throat during practice.