Born in Coatbridge, Scotland, he lived at 77b Whifflet Street. Cunningham was imprisoned for leading a mutiny of the Argyll & Sutherland Highlanders. He led an unemployed march to Brighton in 1933. He worked as a miner.
After going to Spain he served in several units: the Commune de Paris, the No. 1 Company and then the British Battalion. He joined the Machine-Gun Company of Commune de Paris Battalion, XI International Brigade in November 1936. Member of No. 1 Company XIV International Brigade at Lopera.
The small 34 year old played a key role in the February 1937 Battle of Jarama. In order to fight at Jarama one report says that he "left hospital with a fever to go and fight". Wounded Jan. '37 at Los Rozas. Along with Frank Ryan he rallied the remnants of the British battalion in a defensive action which held the line outside Madrid, thereby blocking Franco's attempt to seize the capital. One of the principal military actions of the war, it cost the battalion nearly 500 of the 600 men who had gone into that battle.
Cunningham was hospitalised from March 15 1937 until May 1937 after which he was promoted to Captain. He was sent back to Britain in August 1937 and didn't return to Spain.