Born in Montreal, Quebec, Canada, Sheppard began his career with the Selkirk Fishermen of the Manitoba Junior Hockey League and Edmonton Eskimos of the Western Canada Hockey League. He joined the Detroit Cougars in the team's inaugural season of 1926–27, in which he played 43 games and led the team in goals (13), assists (8), points (21), and penalty minutes (60). On November 22, 1927, Sheppard scored the first goal at the new Detroit Olympia against Ottawa Senators' goaltender Alex Connell. In 310 NHL games, Sheppard scored 68 goals and 58 assists.
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