Born about 1464, he was the seventh son of Sir John Wingfield (1428–1481) of Letheringham, Suffolk, a member of the Privy Council of Edward IV, and Sheriff of Norfolk and Suffolk, and Elizabeth Fitzlewis (d.1500), daughter of Sir John Fitzlewis of West Horndon, Essex, by Anne Montacute.
On 2 July 1509 he is mentioned as a knight, the occasion being a grant to him by Henry VIII, part of the forfeitures of Edmund de la Pole, 3rd Duke of Suffolk.
On 30 Sep Maximilian, hearing that Julius II was ill, appointed Wingfield and the bishop of Gurk his envoys to support the candidature of his nominee at Rome; but, exasperated at being left without money, Wingfield unceremoniously disappeared from the court of Brussels, ostensibly on a pilgrimage, but in reality to join his brother Sir Richard at Calais.
On 18 April 1513 he was again at Brussels, on that day despatched back to the Emperor at Augsburg to secure his support for Henry VIII's scheme of a general confederation against France.
As a reward for his services he had already (14 July) received a joint grant in survivorship with his brother Sir Richard of the office of Marshal of Calais.
The military success of the French in Italy in 1515 meant that Henry was even more eager to bring Maximilian in a confederacy against France.
Henry in reply refused to provide any more money, and expressed his displeasure with Wingfield for having advanced sixty thousand florins to the Emperor on his own responsibility.
Wingfield received the emperor's oath but then heard rumours that Maximilian had secretly subscribed to the obnoxious Treaty of Noyon.
On 5 June, having received instructions from Henry to follow Maximilian back to Germany, Wingfield wrote to the king a point-blank refusal.
Wingfield was nominated (11 April) to the council of war under the Duke of Norfolk, and was at the same time despatched, together with Sir William Fitzwilliam, to the court of Brussels to discuss concerted measures with the regent of the Netherlands.
A series of evasive negotiations followed, and when Henry's projects of a joint invasion of France had given place to an alliance with the French (30 August), Wingfield had explained the change of policy by talking about on the necessity of international peace for the extirpation of Lutheranism.
During the greater part of his life he was an opponent of Lutheranism, but on 25 February 1539, shortly before his death, he wrote Henry a letter praising his ecclesiastical policy and lamenting his own former ignorance.
In 1517 Dirk Martens, Erasmus’s printer, published Wingfield's book entitled Disceptatio super dignitate et magnitudine Regnorum Britannici et Gallici habita ab utriusque Oratoribus et Legatis in Concilio Constantiensi which countered anti-English views in Europe.