In 1514, Wingfield was sent to the Netherlands in order to attempt the arrangement of a marriage between Archduke Charles of Austria and Princess Mary Tudor of England, to secure a dynastic alliance between the Tudors and the rising Habsburgs. But Wingfield's mission failed, and Mary Tudor was married to Louis XII of France in 1514. Wingfield was also occupied in discharging his duties at Calais, but in 1519 he resigned his post there and returned to England.
In 1520, Wingfield was appointed ambassador to the court of Francis I of France. He is known to have helped to arrange the meeting between Henry VIII of England and Francis at the Field of the Cloth of Gold. He twice visited Emperor Charles V in 1521 in an effort to convince him against declaring war on Francis I.
In 1525 Wingfield was sent by Henry VIII on a mission to the Spanish court at Toledo. He died there on 22 July 1525 and was buried at the church of San Juan de los Reyes. His widow was later married first to Sir Nicholas Harvey of Ickworth and secondly to Sir Robert Tyrwhitt of Kettleby.
Family
Wingfield married Catherine, née Woodville, shortly after the 1495 death of her second husband, Jasper Tudor; she was a sister of Queen Elizabeth Woodville.[3] Catherine died in 1497, and Wingfield was a widower for some time. He married in about 1513, his second wife, Bridget Wiltshire, daughter and heiress of Sir John Wiltshire of Stone Castle and Isabella Clothall. They were parents to ten children:
^T.M. Hofmann, 'Wingfield, Thomas Maria (?1516-57), of Stoneley, Hunts. and London', in S.T. Bindoff (ed.), The History of Parliament: the House of Commons 1509-1558 (from Boydell and Brewer, 1982), History of Parliament Online.