Sir Richard Wingfield (c. 1469- 22 July, 1525) was an influential courtier and diplomat in the early years of the Tudor dynasty of England.

He was born at Letheringham, Suffolk to Sir John Wingfield, (c. 1428 - 10 May, 1481) and his wife Elizabeth FitzLewis (c. 1431 - 1497). He was one of twelve or thirteen sons.

He was one of the major landowners in Huntingdonshire and lived at Kimbolton Castle.

Wingfield became a courtier during the reign of Henry VII of England. He married Catherine Woodville sometime after 1495. She was daughter to Richard Woodville, 1st Earl Rivers and Jacquetta of Luxembourg, sister to Elizabeth Woodville, sister-in-law to Edward IV of England and widow to both Henry Stafford, 2nd Duke of Buckingham and Jasper Tudor, 1st Duke of Bedford.

The marriage made him an uncle-by-marriage to Queen consort Elizabeth of York and her husband Henry VII.

He was made Lord Deputy of Calais in 1511. With Sir Edward Poynings and others he was sent in 1512 to arrange a Holy League between Pope Julius II, the English king and other European sovereigns.

Arround 1513, Wingfield was a widower for some time. He married his second wife Bridget Wiltshire , daughter and heiress of Sir John Wiltshire of Stone Castle and Isabella Clothall. They were parents to ten children:

• Charles Wingfield of Kimbolton Castle (1513 - 24 May, 1540). He married Joan Knollys, a sister to Sir Francis Knollys and sister-in-law to Lady Catherine Carey.
• Thomas Maria Wingfield of Stonley Priory. A Member of Parliament. He married first widow Mrs. Margaret Sabyn and secondly Margaret Kerrye.
• James Wingfield of Stone Castle (c. 1519 - 1587?). A politician first known for long-term service to Stephen Gardiner, Bishop of Winchester.
• Lawrence Wingfield.
• Jane Wingfield. Married first Thomas Worlich of Alconbury and secondly Francis Roe.
• Mary Wingfield.
• Margaret Wingfield. She married first Sir Thomas Newman and secondly a son of the Moyle family.
• Cecily Wingfield. She married into the Maidenhead family.
• Elizabeth Wingfield. She married into the Latimer family.
• Catherine Wingfield.

In 1514, Wingfield was went to the Netherlands in order to attempt the arrangement of a marriage between try and arrange a marriage between Archduke Charles of Austria and Princess Mary Tudor of England.

Charles was the eldest son of Philip I of Castile and Joanna of Castile. His paternal grandparents were Maximilian I, Holy Roman Emperor and Mary of Burgundy. His maternal grandparents were Ferdinand II of Aragon and Isabella of Castile.

Mary Tudor was the fifth child and third daughter of Henry VII by Elizabeth of York. Her paternal grandparents were Edmund Tudor, 1st Earl of Richmond and Margaret Beaufort. Her maternal grandparents were Edward IV of England and Elizabeth Woodville.

The marriage would secure the alliance between the Tudors and the rising Habsburg. However Wingfield failed. Mary Tudor was married to Louis XII of France on 9 October, 1514. Charles would succeed his maternal grandfather as Charles I of Spain on 23 June, 1516 and elected Charles V, Holy Roman Emperor on 28 June, 1519.

In the intervals between these and similar errands Wingfield was occupied in discharging his duties at Calais, but in 1519 he resigned his post there and returned to England.

In 1520, Wingfield was appointed ambassador to the court of Francis I of France. He is known to have helped in the arranging the meeting between Henry VIII of England and Francis I at the Field of the Cloth of Gold.

He twice visited Emperor Charles V in 1521 in an effort to convince him against declaring war to Francis I.

Henry VIII created him a Knight of the Garter on 1522. The future Ferdinand I, Holy Roman Emperor was the only other Knight created during that year. Wingfield was made Chancellor of the Duchy of Lancaster in 1524. For his services Wingfield was granded lands throughout the Kingdom of England. Notably Kimbolton Castle which was further expanded by him.

While on an Errand to the Spanish court, Wingfield died at Toledo on 22 July, 1525. He is buried at St John de Pois in that city. His widow was later married first to Sir Nicholas Harvey of Ickworth and secondly to Sir Robert Tyrwhitt of Kettelby.