By 1509, when Sir John died, Anthony had been appointed Esquire of the body, and he attended the funeral of Henry VII. Wingfield first saw active service in the first war of Henry VIII's reign, fighting at the siege of Tournai in 1513. He was knighted in 1513 for his part in the capture of Tournai. He was appointed High Sheriff of Norfolk and Suffolk for 1515–16. He attended the Field of the Cloth of Gold in 1520, and served in the 1523 French campaign of Charles Brandon, the Duke of Suffolk; and lastly in the 1544 capture of Boulogne.