He came to Ireland as a military adventurer in the latter part of the 16th century and afterwards fought in
Flanders, France and
Portugal, gaining the military rank of
lieutenant colonel. Returning to Ireland, Wingfield distinguished himself and was wounded in an expedition against
Tyrone, and was knighted by the
Lord Deputy,
William Russell, in
Christ Church Cathedral on 9 November 1595. He served as a
colonel in the expedition against
Calais, and in 1600 was advanced to the office of
Marshal of Ireland, with a retinue of fifty horse and a company of foot. In 1601 during the
4th Spanish Armada, he led a force at the
reduction of Kinsale, and was one of those who signed the articles of capitulation made between the
Lord Deputy of Ireland and Don
Juan del Águila, commander of the Spanish troops made prisoners on that occasion. ==O'Doherty's Rebellion==