[2] Born in Hartlepool, County Durham, Brackstone played in the Middlesbrough youth system as a trainee before signing a professional contract on 7 July 2000.
[1] After being deemed surplus to requirements at Middlesbrough he signed for Third Division team York City on 27 February 2002 on a contract until the end of the 2001–02 season following a trial.
[6][7] Brackstone scored a direct free kick from 20 yards in stoppage time to give York a 2–2 draw with Bristol Rovers on 19 October.
[8] He suffered a back injury in October and after a late fitness check missed a game against Wrexham, eventually making his return in a 0–0 draw at Hartlepool United.
[9][10][11] He had an operation to remove his appendix after being taken to hospital following his substitution against Lincoln City in December and after being expected to be out of action for six weeks he made his return in a 1–0 victory over Bournemouth on 15 March 2003.