Wakeford joined the Royal Air Force (RAF) in 1941. After flight training with the US Navy at Naval Air Station Pensacola in Florida, he joined Coastal Command to fly anti-submarine missions. He flew Catalina flying boats with No. 212 Squadron for 18 months from November 1942, patrolling the Indian Ocean from its base in Karachi. After a period training other pilots of flying boats, he joined No. 210 Squadron in October 1944, based at Sullom Voe in the Shetland Islands, patrolling the Norwegian Sea. He flew in support of Russian convoys and intercepted German submarines based in Norway.