Stein worked as a coalminer while playing football part-time for Blantyre Victoria and then Albion Rovers. He became a full-time professional football player with Welsh club Llanelli Town, but returned to Scotland with Celtic in 1951. He enjoyed some success with Celtic, winning the Coronation Cup in 1953 and a Scottish league and Scottish Cup double in 1954. Ankle injuries forced Stein to retire from playing football in 1957.