Freestone joined Middlesbrough from Nottinghamshire club Arnold Town of the Northern Counties (East) League midway through the 1994–95 season.
Before joining Boro for a small fee he had netted 54 goals for Arnold Town and had trials with Leeds United, Nottingham Forest, Notts County and Chesterfield.
After a loan spell, Freestone joined Northampton in December 1997 scoring 20 goals including a hat trick against Plymouth Argyle.
[5] After leaving Northampton, Freestone signed for Hartlepool United and scored the 2 goals against Scarborough that kept them in the Football League.
[9][10] He was appointed joint manager of Arnold Town alongside Martin Carruthers two games into the 2009–10 season.