Fleetwood came from a cadet branch of the Lancashire family which held for three generations an office in the court of wards worth £1,500 p.a. His father, a zealous Puritan in religion but a moderate in politics, sat for Hindon in the Long Parliament till his death in 1641; but Fleetwood, already a courtier, had been involved in a double return at Woodstock, which he had represented in the Short Parliament, and never took his seat. ‘Being a servant in ordinary of the late King, he attended his person at Oxford’, bringing with him, as he later claimed, £60,000 revenue from the court of wards. Parliament naturally removed him from his post, which was given to his brother Charles, later a general during the Interregnum. From his father he inherited, beside his office, only a small estate in Northamptonshire bought under James I which he valued at £300 p.a., but he had also a grant for life of Woodstock Park, worth another £120 p.a. He was allowed to compound on the Oxford Articles for £510, which was paid, or at least promised, by his brother.4H. W. Bell, Court of Wards, 25; Keeler, Long Parl. 178-9; G. E. Aylmer, King’s Servants, 381; SP23/196/165-7; VCH Northants. iii. 165; Cal. Treas. Bks. iv. 471-2; Cal. Comm. Comp. 1403.
Fleetwood was awarded £2,000 compensation by the Convention for the abolition of the court of wards, but no provision was made for payment. He was returned for Woodstock in 1661; and listed as a friend by Lord Wharton. A moderately active Member of the Cavalier Parliament, he was named to 94 committees. In the opening session he was appointed to the committees to inquire into the shortfall in the revenue and to consider the corporations bill, and had the rather empty satisfaction of hearing that his compensation ought to be doubled. He was listed as a court dependant in 1664 and named to the committee for the conventicles bill, though his brother was a leading light in the Independent congregation of Dr John Owen at Stoke Newington. He was one of the Members ordered to bring in a supplementary militia bill on 3 Apr. 1668. His name appears on both lists of the court party in 1669-71 and on the Paston list as a court dependant. But on his deathbed he complained that lack of compensation for loss of office ‘and his great losses in the late unhappy times have forced him to contract great debts’. He was recommended as ‘a fit object of favour’ on 2 Feb. 1674, but died before anything could be done for him. He was buried at Aldwinkle All Saints ten days later.5CJ, viii. 219, 407; Bell, 165; Cal. Treas. Bks. iv. 471-2.