Skipwith was educated at Eton College and at Trinity College, Cambridge. In 1801 he married Harriett, the daughter of Gore Townsend of Honington Hall, Warwickshire and granddaughter of the 4th Earl of Plymouth; they had 12 sons and 8 daughters. His younger brothers inherited his father's estates in Virginia, but Grey inherited the estates of his relative Sir Thomas Skipwith, 4th Baronet, including Newbold Revel.
At the 1831 general election he was elected as a Member of Parliament (MP) for Warwickshire. When the county was divided in 1832 he was elected for the new Southern division of Warwickshire. He stood down in 1835, and then unsuccessfully contested two by-elections: South Warwickshire in 1836 and North Warwickshire in 1837.
- Leigh Rayment's list of baronets – Baronetcies beginning with "S" (part 2)
- Escott, Margaret (2009). D.R. Fisher (ed.). "SKIPWITH, Sir Gray, 8th bt. (1771-1852), of Alveston Villa, nr. Stratford-upon-Avon, Warws. and 6 Pall Mall East, Mdx". The History of Parliament: the House of Commons 1820-1832. Cambridge University Press. Retrieved 7 June 2014.