Cherry played junior hockey with the Barrie Flyers and the Windsor Spitfires in the Ontario Hockey Association. Cherry won the Memorial Cup while playing defence in Barrie in 1953. He dropped out of high school, and in 1954 he signed with the American Hockey League’s (AHL) Hershey Bears.

Cherry had a long playing career in professional minor hockey, and in 1955 played his only NHL game when the Boston Bruins called him up during the playoffs. According to Cherry, a baseball injury suffered in the off season kept him from making the NHL, despite his almost 20 years playing in the minor leagues.

Cherry won the Calder Cup championship (AHL) four times—1960 with the Springfield Indians, and 1965, 1966, 1968 with Rochester. He also won the Lester Patrick Cup, the Western Hockey League Championship, with the Vancouver Canucks in 1969.

He retired as a player in 1970, but came out of retirement two years later to play 19 final games with the Rochester Americans. 

Cherry was inducted into the American Hockey League Hall of Fame in 2019.

Source: https://en.wikipedia.org/wiki/Don_Cherry#Regular_season_and_playoffs