He was born at Letheringham, Suffolk to Sir John Wingfield (c. 1428 – 10 May 1481) and his wife Elizabeth FitzLewis (c. 1431-1497). He was the eleventh of twelve sons; and brother to Humphrey Wingfield. His paternal grandparents were Sir Robert Wingfield and Elizabeth Gousell. He was one of the major landowners in Huntingdonshire and lived at Kimbolton Castle.
Wingfield became a courtier during the reign of Henry VII of England. He married Catherine Woodville sometime after 1495. She was daughter to Richard Woodville, 1st Earl Rivers and Jacquetta of Luxembourg, sister to Elizabeth Woodville, sister-in-law to Edward IV of England and widow of both Henry Stafford, 2nd Duke of Buckingham, and Jasper Tudor, 1st Duke of Bedford. The marriage made him an uncle-by-marriage to Queen consort Elizabeth of York and her husband Henry VII.
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 in the arranging 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.
Henry VIII created him a Knight of the Garter in 1522. The future Ferdinand I, Holy Roman Emperor was the only other Knight created during that year. Wingfield was made Chancellor of the Duchy of Lancaster in 1524. For his services Wingfield was granted lands throughout the Kingdom of England, notably Kimbolton Castle which was further expanded by him.
While on an errand to the Spanish court, Wingfield died at Toledo on 22 July 1525. He is buried at St John de Pois in that city. His widow was later married first to Sir Nicholas Harvey of Ickworth and secondly to Sir Robert Tyrwhitt of Kettleby.
His first wife Catherine, née Woodville, sister of Queen Elizabeth Woodville, 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:
- Charles Wingfield of Kimbolton Castle (1513 – 24 May 1540). He married Joan Knollys, a sister to Sir Francis Knollys and sister-in-law to Lady Catherine Carey.
- Thomas Maria Wingfield of Stonley Priory. A Member of Parliament. He married first widow Mrs. Margaret Sabyn and secondly Margaret Kerrye.
- Jacques Wingfield of Stone Castle (c. 1519-1587?). A politician first known for long-term service to Stephen Gardiner, Bishop of Winchester.
- Lawrence Wingfield.
- Jane Wingfield. Married first Thomas Worlich of Alconbury and secondly Francis Roe.
- Mary Wingfield.
- Margaret Wingfield. She married first Sir Thomas Newman and secondly a son of the Moyle family.
- Cecily Wingfield. She married into the Maidenhead family.
- Elizabeth Wingfield. She married into the Latimer family.
- Catherine Wingfield.
- This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). Encyclopædia Britannica (11th ed.). Cambridge University Press.
- Powerscourt, Mervyn: Muniments of the Ancient Saxon Family of Wingfield, London 1894, page 22
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