His first command was a World War I submarine, the "H28", in which he patrolled off the coast of the Netherlands. This was followed by the newly built but ill-fated "Umpire" which sank in the North Sea after a night time collision in July 1941 with an armed British trawler, the "Peter Hendriks". Wingfield, picked up semi-conscious from the North Sea forty minutes later, was the only survivor of the four men who had been on the bridge. Of those men trapped in the hull who escaped, one was Edward Young who described the incident in his book ‘One of Our Submarines’. Wingfield was then given command of the submarine "Sturgeon" which made two Arctic patrols. In one of these he penetrated Trondheim fjord submerged, despite the presence of mines, and sunk a merchant ship, for which he received a DSO. Between these patrols "Sturgeon" acted as a navigating beacon for the raid on St. Nazaire in March 1942.