From 1955 until 1964, the Waterloo Siskins won the league six out of nine seasons, losing out to Burlington in 1957 and 1958 and the Owen Sound Greys in 1961. Neither Burlington or Owen Sound managed to win the Sutherland Cup with their league championship, in fact only Owen Sound even made to the finals where they were swept by the St. Michael's Buzzers of the Metro Junior B Hockey League. During that streak, the Waterloo Siskins won the Sutherland Cup four times. In 1956 they defeated the Brampton Regents of the Metro league 4-games-to-1 with 1 tie. In 1960, the Siskins defeated the Marlboros of the Metro League 4-games-to-2 with 1 tie to win the provincial crown. In 1962, they defeated the St. Thomas Elgins of the Western Junior B League 4-games-to-1 and in 1964 they defeated Weston of the Metro League 4-games-to-1 to claim another crown.