Born in Galston, Ayrshire, Cunningham began his career with local Junior side Newmilns[3] before moving to Kilmarnock in 1909.
He won seven League titles and played in Rangers' famous 1928 Scottish Cup Final triumph where they defeated Celtic 4–0 to win the trophy for the first time in 25 years.
[8] Cunningham moved to Newcastle United in 1928, becoming the then oldest player to make his debut in the English football League at the age of thirty-eight.
Technically, he was the first true manager of the club, as his predecessor Frank Watt had no control over team selection.
After his time with Newcastle, he returned to Scotland where he managed Dundee between 1937 and 1940 before becoming a sports writer after World War II.