Returning to England with his wife and newly born child, Wingfield served as master of the ordnance under Sir John Norris in Brittany against the forces of the Catholic League in 1591, and the following year he is mentioned as being in charge of the storehouse at Dieppe.
Ordered on 21 June to bait an ambush, Wingfield led 200 men along the isthmus leading to the city gates which were defended by 500 Spanish cavalry.
In the rout that followed the English broke through the city gates and Wingfield was wounded in the thigh, while Essex and a small band fought through to the plaza.
Unable to walk, Wingfield captured a horse to follow Essex, and—now an obvious target—was killed instantly by a bullet to the head just as the city surrendered.
He was buried five days later with all the funerall solemnities of warre in the cathedral at Cadiz, while the generals threw their handkerchiefs wet from their eyes into the grave (Stow).