Cunningham's interest in Paralympic sport stemmed from his time at Shenton Park Rehabilitation Centre where he witnessed residents training for the International Stoke Mandeville Games. He participated at the 1960 Rome Games, in wheelchair fencing and wheelchair basketball. He was not selected for 1964 Tokyo Games due to an injury in selection trials in Adelaide. He participated in the 1968 Tel Aviv Games in men's slalom C in athletics and wheelchair basketball. Cunningham won silver medals in both of these events.