15 June Wingfield wrote from Brussels that Charles would accept mediation provided restitution were made. On 22 June the emperor requested Wingfield to return to England and present to Henry a memorial of his case against Francis. It is apparent from the emperor's language that Wingfield had ingratiated himself with him as successfully as he had done with Francis I and Louise of France. He left Brussels on 22 June. But a few days after his return to England two envoys from the emperor arrived with the intelligence that Charles had reverted to his first mind and claimed Henry's aid in active hostilities against the French. Wolsey remarked that ‘Wingfield's despatch disagreed with their charge,’ and resolved to send Wingfield back again to persuade Charles to a more pacific temper. Wingfield arrived at Antwerp on 10 July 1521, accompanied by the emperor's two envoys, and found Charles still bent on an invasion of France, and still insisting on the active aid of England. By 22 July Wingfield seems to have become aware that Wolsey's secret intention was to cajole Francis, and prepare to act with the emperor. Towards the end of October Wolsey sent Sir Thomas Boleyn and Sir Thomas Docwra to Charles to solicit him to enter into a truce with France; they were instructed to take Wingfield's advice on the method of executing their mission. The three ambassadors followed the emperor to Courtrai on 24 Oct. In the same month Knight was appointed to succeed Wingfield, but the latter still remained at Oudenarde with his two colleagues, wrestling with the emperor's obstinate refusals of truce, and writing almost daily despatches to Wolsey, who was determined not to let him go until some conclusion was brought to the negotiations. About 16 Dec. Wingfield and Spinelly, who acted as his colleague after the departure of Boleyn and Docwra on 17 Nov., accompanied the emperor to Ghent. At last, on 8 Jan. 1522, the emperor himself requested Wingfield to leave at once for England upon a diplomatic mission. Wingfield replied, as he had done on the similar occasion in the previous June, that for him to leave his post without Henry's permission would be a breach of rule; but, as before, he consented, Charles explaining to Henry the circumstances of the case. Charles further requested Wolsey to bestow the Garter upon Wingfield, and announced his intention of pensioning him. Wingfield's promotion to the Garter took place in the following year (Anstis, ii. 232). He returned to Antwerp on 4 May 1522, with instructions to persuade the emperor to accept Wolsey's offer of mediation. He was also to arrange for the emperor's visit to England on his way to Spain. Wingfield probably accompanied Charles, who reached Dover on 26 May 1522. His services were now employed by Henry upon a commission under the Earl of Surrey, lord high admiral, for recruiting the royal navy by impressing ships of the merchant service and certain Venetian vessels to act as convoy for the emperor's voyage to Spain. He also accompanied the fleet which burnt Morlaix and the English army on its incursion into France. At the end of 1523 Wingfield probably returned to England with Suffolk and the principal military commanders.
Wingfield utilised the opportunity of his return to claim and receive rewards for his services. On 20 Nov. 1522 he was granted the castle and manor of Kimbolton, and on 1 Sept. 1523 the neighbouring manor of Swyneshede, lands in Swyneshede and Tylbrook, Huntingdonshire, the manor of Hardewyke, and lands in Hardewyke, Overdene, and Netherdene, Bedfordshire, also forming part of the late Duke of Buckingham's forfeited estates. At Kimbolton he built ‘new fair lodgings and galleries’ (Leland, Itin. v. 2). On 14 April 1524 he was made chancellor of the duchy of Lancaster. In the course of the years 1523–4 he was nominated upon the commission of the peace for no fewer than twenty-five southern and midland counties. Wingfield had, according to his friend Hugh Latimer, ‘a regard for literary men.’ On the death (25 May 1524) of Sir Thomas Lovell [q. v.], high steward of the university of Cambridge, Wingfield solicited Henry's influence to procure him the post. The university had promised it to Sir Thomas More, but at the king's instance More withdrew his candidature and Wingfield was appointed. ‘Who,’ wrote Latimer to Dr. Grene, master of St. Catharine's, ‘has more influence with the king than Wingfield?’
On 24 Feb. 1525 Francis I was defeated and captured at the battle of Pavia. At the end of March Wingfield and Tunstall were despatched by Henry to Spain [see under Tunstall, Cuthbert]. During this embassy Wingfield died at Toledo on 22 July 1525 (Inq. post mortem), and was buried by his own request at the church of the friars observants, San Juan de los Reyes.
Wingfield married, as her third husband, Katherine, daughter of Richard Woodvile, earl Rivers [q. v.], widow of Henry Stafford, duke of Buckingham [q. v.], and afterwards of Jasper Tudor, duke of Bedford [q. v.] This double connection with the king accounts for the confidence reposed in him. The marriage also supported his claims to share in the forfeited Buckingham estates.
