Before Cherry was a coach, he played hockey as a professional minor league defenceman for 16 seasons, beginning in 1954. He was recruited to play one game for the Boston Bruins during the Stanley Cup finals against the Montreal Canadiens in 1955, but an off-season injury prevented him from returning to the NATIONAL HOCKEY LEAGUE (NHL). Cherry first retired from hockey in 1969 after spending 6 seasons with the Rochester Americans in the American Hockey League (AHL), but he returned to the team in 1971, first as a player and in Jan 1972 as head coach.