Bergman joined the Detroit Red Wings for the 1964–65 season and looked very comfortable as a freshman. In 58 games, Bergman held back his offensive instincts while focusing on his defensive work. Gradually he gained confidence and seniority on the team. He played solidly when the Wings reached the 1966 Stanley Cup finals and lost to the Montreal Canadiens in six games. Bergman was the man tangled up with Montreal’s Henri Richard when Richard scored the Stanley Cup-winning goal against Detroit in overtime during Game 6 of the 1965–66 final series. Bergman, like all Wings from that season, was convinced Richard pushed the puck in with his glove and the goal should not have counted. He said this after the game,