Jolliffe was the son of Reverend William John Jolliffe, the son of William Jolliffe and his wife Eleanor Hylton, daughter and heir of Sir Richard Hylton, 5th Baronet (who had assumed the surname of Hylton in lieu of his patronymic Musgrave; see Musgrave Baronets) and his wife Anne, sister and co-heiress of John Hylton, de jure 18th Baron Hylton.[citation needed] Jolliffe first served in the Army and achieved the rank of captain in the 15th Dragoons. He notably took part in the events at St Peter's Field in Manchester in 1819 (the "Peterloo Massacre").[1] In 1821, at the age of twenty, Jolliffe was created a Baronet, of Merstham in the County of Surrey.[2]