Career
Cunningham earned a soccer scholarship to Division 1 Big east University West Virginia University and played college soccer with the West Virginia Mountaineers, for 4 years before playing professionally in England for Fisher Athletic and in Australia for Sorrento. In 2011 Cunningham was named club captain of Balestier and has led Balestier to a record finish in the 2013 South.League season.Cunningham was 1 of 5 players Shortlisted for player of the season in 2013 and eventually lost out to Korean Marquee signing Lee Kwan Woo. Cunningham has stated that he wants to play for Singapore at international level