He married twice: firstly Lady Margaret Cave, the daughter of Roger Cave of Stanford, Northamptonshire. They had four sons and four daughters. His second wife was Jane, the daughter of John Roberts and the widow of John Markham of Sidebrook. His eldest son was Sir Henry Skipwith.
Skipwith was knighted on 21 April 1603 at Worksop Manor by King James I, who was travelling to London following the Union of the Crowns.[4] He returned to Worksop on 18 June to meet Anne of Denmark at Worksop, and she and her son Prince Henry went on to stay in his house at Leicester on 23 June, despite fears of plague.[5]Princess Elizabeth stayed at the house of Mr Pilkington, sleeping in sheets borrowed from a house at Elmesthorpe. Anne of Denmark and Prince Henry were given silver cups by the town council. The cups were bought in London from William Herrick (a goldsmith with a Leicester background), and then engraved with the royal arms. Prince Henry's cup was smaller. Princess Elizabeth arrived separately in Leicester and was given claret, white wine, and Rhenish wine, with a sugar loaf weighing 9 pounds 10 ounces. She was nearly 7 years old.[6]
^Helen Stocks, Records of the Borough of Leicester, vol. 3 (Cambridge, 1923), pp. 20-1.
^Walter Seton, 'Early Years of Henry Frederick, Prince of Wales, and Charles, Duke of Albany', Scottish Historical Review, 13:52 (July 1916), pp. 373-4.