Willson started out in junior hockey with the Newmarket Redmen and St. Michael's Majors from 1931 to 1934. He won back-to-back Memorial Cups with the Redmen in 1933 and the Majors in 1934. In 1934-35 he played with the senior Oshawa Chevrolets. In 1935 Willson went to Great Britain to join the Earls Court Rangers and played there for three seasons. In 1937 he returned to North America. He played for the senior Verdun Maple Leafs of the Quebec Senior Hockey League, making the First All-Star team. Willson also got into 18 games for the Montreal Canadiens.
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