Marriage and family
Dudley was married at the age of 14 to Theodosia Harington (d. 1649). She was the daughter of James Harington of Exton, Rutland, a lawyer and long-serving MP. The Haringtons were the most important landowners in Rutland and Theodosia's eldest brother, John, was created Baron Harington of Exton in 1603. Dudley and Theodosia had a son and four daughters:
Sir Ferdinando Sutton (1588-1621), who married Honora Seymour, a daughter of Edward Seymour, Viscount Beauchamp, who was considered by some a potential claimant to the throne on the death of Elizabeth I.
Mary Sutton (1586–1645), who married Alexander Home, 1st Earl of Home.
Anne Sutton (1589-1615), who married Hans Meinhard von Schönberg, the Palatine Ambassador to England: their son was Frederick Schomberg, 1st Duke of Schomberg.
Margaret Sutton (1597-1674), who in 1627 married Sir Miles Hobart, Knight of the Bath, of Fleet Street in the City of London and of Little Plumstead in Norfolk, a son of Henry Hobart of Plumstead by his wife Willoughby Hopton, a daughter of Arthur Hopton of Blythburgh and Witham. They had sons Edward, Miles, Tom, John and James, and a daughter Willoughby. She was buried at St Margaret's, Westminster.
Theodosia Sutton (1599-1615).
Lord Dudley also had a longtime mistress Elizabeth Tomlinson, who bore him a large family of illegitimate children, at least 11 in number. Lord Dudley provided for this second family. The eldest Robert Dudley otherwise Tomlinson was given a small estate at Netherton in Dudley. Another son Dud Dudley was given a lease of Chasepool Lodge in Swindon, Staffordshire. A daughter Jane was grandmother to ironmaster Abraham Darby I. A John Dudley who features in the diary of Lady Anne Clifford may have been a son of Elizabeth Tomlinson.
At the Star Chamber, Gilbert Lyttelton attempted to discredit Dudley by claiming that he had abandoned his wife in London without support to live with Elizabeth Tomlinson, "a lewd and infamous woman, a base collier's daughter". The Privy Council ordered Dudley to pay his wife an allowance, which he failed to do. In August 1597 he was sent to Fleet Prison. He was released after a few days, on condition that he pay maintenance of £100 annually for his wife, and £20 for each legitimate child. In less than 18 months he was back before the Privy Council, having got into arrears.
Dudley's legitimate son, Ferdinando, predeceased him, leaving a daughter Frances. Dudley married this granddaughter to Humble Ward, the son of a wealthy goldsmith, William Ward, who was one of his creditors.
Dudley died on 23 June 1643 and was buried in St Edmund's Church, Dudley. Frances Ward inherited the estates, with their debts, and became Baroness Dudley suo jure. Humble Ward paid the debts and redeemed the estates for the benefit of themselves and their descendants.