 Born in Galston, Ayrshire, Cunningham began his career with local Junior side Newmilns FC before moving to Kilmarnock in 1909.After six seasons at Rugby Park he joined Rangers in 1915.He made his Rangers debut on 5 April 1915 in a 1–0 defeat to Partick Thistle, and made five appearances in his first season at Ibrox.