Born in Warter-on-the-Wolds, Yorkshire, he was the second son of Sir Henry Stapleton of Wighill (Wighill, Yorkshire, 1572 – St. Andrews, 16 February 1630/1631) and wife Mary Forster (Bamborough Castle, Northumberland, 30 March 1569 – St. Andrew Holborn Parish, London, Middlesex, 6 November 1656).
When the civil war broke out he was made a colonel of horse and commander of the Earl of Essex's bodyguard.
He commanded a brigade of cavalry at the Battle of Edgehill, one of two held in reserve until late in the day and whose charge against the flanks and rear of the Royal infantry almost secured a parliamentary victory but proved ultimately inconclusive.
[citation needed] However, he fell out of favour when he opposed the Self-Denying Ordinance and the advancement of Oliver Cromwell.
[citation needed] Stapleton married twice, first in 1627 to Frances Hotham (1605–1636), daughter of Sir John Hotham, 1st Baronet, and wife Katherine Rodes, widow of John Gee, Esq., of Beverley (1606–1627), with issue, by whom he had two sons: His second wife was Barbara Lennard (Hurstmonceaux, Sussex, 1 April 1604 – ca.