Cain was born in Newmarket, Ontario to John (Jack) and Elizabeth "Eliza" Cain (née Currier). He played junior hockey for the Newmarket Redmen and the Hamilton Tigers of the OHA.\n', '

Cain\'s NHL career started when he joined the Montreal Maroons of the NHL in the 1933–34 season. He split that season between the Maroons and the Hamilton Tigers of the OHA. In 1934–35 Cain briefly played for the Windsor Bulldogs of the IHL. With the exception of a one-game stint with the Hershey Bears in 1940–41, he would remain in the NHL for the next 11 seasons.\n', '

As a member of the Maroons, Cain played on a line with Gus Marker and Bob Gracie. They were dubbed the "Green Line" and their combined offensive prowess led Montreal to their second Stanley Cup Championship in 1934–35. Cain was dealt to the Montreal Canadiens in the fall of 1938. After one season in Montreal, he was traded to the Boston Bruins for Charlie Sands and Ray Getliffe.\n', '

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