Leonard Digges, born about 1515, was the only son of James Digges (born c.1473), esquire, of Digges Court and Broome in Barham, Kent, by his second wife, Philippe Engham, the daughter of John Engham, esquire, of Chart, Kent. James Digges had been High Sheriff of Kent in 1510–11, and had married as his first wife Mildred Fineux, the daughter of Sir John Fineux, Chief Justice of the King's Bench, and Elizabeth Apuldrefield, by whom he had an only son, John Digges, who married Mildred Scott, the daughter of Sir John Scott (d. 7 October 1533) of Scot's Hall in Smeeth, Kent. John Digges predeceased his father, leaving two sons by his wife, Mildred Scott, William Digges and Francis Digges. James Digges made his last will on 20 February 1535/6 requesting burial in the north chancel of the church of Barham, 'where my mother and my wife do lie', and naming as executors his second wife, Philippe; John Sackville, esquire; his nephew, Robert Brent, gentleman; and his son, Leonard, with Sir William Hawte as overseer. The will was proved on 24 November 1540, at which time his second wife, Philippe, was still living.