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In 1587 he was again sent to the Low Countries, with his friend Lord Buckhurst and Sir John Norris, in order to allay the discontent which had been excited by the Earl of Leicester's proceedings in Holland, and to open the way for a peace with Spain.
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.