He was son of Sir Robert Wingfield senior(c. 1370 – 3 May 1409) and Elizabeth Russell. (Letheringham, which is near Wickham Market and Easton, Suffolk, was the site of a small priory which passed to Sir Anthony Wingfield at the Dissolution. The church, which became ruinous in the 18th century and was afterwards restored, contained early Wingfield memorials.)
On 19 May 1426, Robert was knighted at Hereford by King Henry VI of England. From 1427 to 1436 he was knight of the shire for Suffolk. On 28 November 1436, Robert was appointed Steward of the Honour of Richmond in Norfolk.
In 1443 he became Steward to John de Mowbray, 3rd Duke of Norfolk and accompanied the Duke on his embassy to the court of King Charles VII of France. He was accused of rioting in 1447 and imprisoned in the Marshalsea, but pardoned in 1448. He was appointed knight of the shire for Hertfordshire in 1449.
Marriage and children
He was married before 18 August 1421 to Elizabeth Goushill or Gousell (1396–1491), daughter of Sir Robert Goushill or Gousell of Hoveringham, Nottinghamshire, and Elizabeth FitzAlan. They were parents to thirteen children:
- Richard Wingfield (c. 1428 – before 1509).
- Sir John Wingfield of Letheringham, Suffolk (c. 1430 – 10 May 1481), High Sheriff of Norfolk and Suffolk, Member of Parliament under both Henry VI and Edward IV of England. Knight of the Bath. He married Elizabeth FitzLewis. They were parents of ten children, including Richard Wingfield.
- Sir Robert Wingfield (c. 1432). Comptroller for Edward IV. Member of Parliament, representing Hertfordshire. Married Anne Harling.
- Sir Henry Wingfield of Orford, Suffolk (c. 1435 – May 1493/1494). Served the House of York during the Wars of the Roses. Knighted by Edward IV for his accomplishments during the Battle of Tewkesbury (4 May 1471). Appointed Governor of Orford Castle. Married first Alice Seckford and secondly Elizabeth Rookes. Ancestor of the Wingfields of Tickencote.
- Sir Thomas Wingfield (c. 1438 – 1475). Knighted by Edward IV for his accomplishments during the Battle of Tewkesbury. Married Philippa Tiptoft, daughter of John Tiptoft, 1st Baron Tiptoft and Joyce Charleton and widow of Thomas de Ros, 9th Baron de Ros of Helmsley and remarried as his third wife to Edward Grimston.
- William Wingfield (c. 1440 – 1509).
- Elizabeth Wingfield (c. 1441 – 28 April 1497). She married in 1462 Sir William Brandon of Wangford, Suffolk and of Soham Court, Suffolk (1425 - 4 March 1491). They were grandparents to Charles Brandon, 1st Duke of Suffolk.
- Anne Wingfield.
- Katherine or Catherine Wingfield (born c. 1444). Married Sir John Bonville of Halnaker, Sussex. Daughter Florence Bonville (1472 - October 1524) married without children Sir Humphrey Fulford and John Bourchier, 1st Earl of Bath.
- Anthony Wingfield of Glossop, Derbyshire (born c. 1446). Married Mary Duke. Ancestor of the Wingfields of Onslow.
- Agnes Wingfield (born c. 1448). Married John de Fremingham.
- Alice Wingfield.
- Margaret Wingfield.
- G. E. Cokayne; with Vicary Gibbs, H.A. Doubleday, Geoffrey H. White, Duncan Warrand and Lord Howard de Walden, editors. The Complete Peerage of England, Scotland, Ireland, Great Britain and the United Kingdom, Extant, Extinct or Dormant, new ed., 13 volumes in 14 (1910-1959; reprint in 6 volumes, Gloucester, U.K.: Alan Sutton Publishing, 2000), volume II, page 16.
- Charles Mosley, editor. Burke's Peerage, Baronetage & Knightage, 107th edition, 3 volumes (Wilmington, Delaware, U.S.A.: Burke's Peerage (Genealogical Books) Ltd, 2003), volume 3, page 3199.