Fleetwood was born in Gloucester, Gloucestershire. As a youngster Fleetwood was a talented rugby union fly-half and was part of the Newent team that won the Gloucester Schools Cup.
Fleetwood's early life and sporting prowess were highlighted by his birth in Gloucester, Gloucestershire, where he excelled as a rugby union fly-half while playing for the Newent team that won the Gloucester Schools Cup.