On the death of his father in 1570, Fleetwood, then aged about nine, inherited £50 plus an annuity of £13 6s. 8d. Before reaching his majority Fleetwood also became a beneficiary of one of his numerous older brothers, who left him some household stuff and shares in the Mineral and Battery Company.
Fleetwood represented Chipping Wycombe in the last Elizabethan Parliament, and was re-elected there in 1604. His only committee appointment was to consider a bill for payment of Crown debts (2 May 1607).
After the dissolution of Parliament in early 1611 Fleetwood obtained recurrent letters of protection against his creditors.
