Wentworth married firstly, Anne Say (died before 22 October 1494), the daughter of Sir John Say and Elizabeth Cheyney, by whom he had two sons and four daughters:[4][5][6][7]
Sir Richard Wentworth, who married Anne Tyrrell, the daughter of Sir James Tyrrell, by whom he had three sons, Thomas Wentworth, 1st Baron Wentworth, Richard and Philip, and five daughters, Anne, Elizabeth, Margery, Dorothy and Thomasine.[8]
Edward Wentworth.[8]
Elizabeth Wentworth (died after 22 September 1545), who married firstly, Sir Roger Darcy (d. 30 September 1508) of Danbury, Essex, by whom she was the mother of Thomas Darcy, 1st Baron Darcy of Chiche (1506 – 28 June 1558).[9][5] She married secondly, as his second wife, Sir Thomas Wyndham (d.1522) of Felbrigg, Norfolk,[10] Vice-Admiral and councillor to Henry VIII, by whom she was the mother of Sir Thomas Wyndham.[11] She married thirdly, as his third wife, John Bourchier, 1st Earl of Bath.[12][11]
Margery Wentworth (c. 1478 - c. October 1550), who married, before 1500, Sir John Seymour, by whom she was the mother of Jane Seymour, third wife of Henry VIII and mother of Edward VI.[13][14][15][5]
Dorothy Wentworth, who married, as his second wife, Sir Robert Broughton.[8]