He appears to have acted in 1518, together with his eldest brother, Sir John Wingfield, as a financial agent between the government and the Duke of Suffolk.
On 11 June 1529 he was nominated by Wolsey one of a commission of twenty-one lawyers presided over by John Taylor to hear cases in chancery, and on the following 3 November he was returned to parliament for Great Yarmouth.
In this capacity he, sitting with three other commissioners at Woodbridge, Suffolk, returned a verdict on 19 September that the college and its lands were forfeited to the king.
During his speakership were passed the acts severing the church of England from the Roman obedience and affirming the royal supremacy; Wingfield supported Henry's policy.
For these services he was rewarded by a grant in tail male, dated 29 June 1537, of the manors of Netherhall and Overhall in Dedham, Essex, and all the lands in Dedham belonging to the suppressed nunnery of Campsey, Suffolk, also of the manor of Crepinghall in Stutton, Suffolk, and all lands there belonging to the late priory of Colne Comitis (Earls Colne) in Essex.
After the conviction of Henry Courtenay, 1st Marquess of Exeter he received a grant of a lease of his lands in Lalford Says, Ardelegh, Colchester, and Mile-End, in Essex and Suffolk.
[2] Wingfield married between 1502 and 1512 Anne, daughter and heiress of Sir John Wiseman of Essex, and widow of Gregory Adgore, Edgore, or Edgar, serjeant-at-law.
His son and heir, Robert, married Bridget, daughter of Sir Thomas Pargeter, knt., alderman and lord mayor of London in 1530.