He then brought in a number of new players, including Luton's home grown starlet Matthew Taylor, and this pushed Pitt out of the first-team squad.

Returning to the starting line-up in the following match, a 3–0 loss at Oldham Athletic, Pitt remained in the team for the next five matches on the left-hand side of midfield as the side continued their good home form with 3–1 victories over both Tranmere Rovers and Wycombe Wanderers, but also saw their away form cost them with a 2–2 draw at Swindon Town and losses at Brentford (4–2) and AFC Bournemouth (6–3).

In late October, following the heavy loss at Bournemouth, manager Mike Newell decided to allow Pitt to return to Portsmouth.

Wanting to sign an experienced goalkeeper, Newell took the decision to allow Pitt to return to Portsmouth with his thanks for his efforts during his time at Kenilworth Road.

[8] He made his debut as a 75th-minute substitute in a 1–0 defeat at Ebbsfleet United on 13 February, nearly scoring an equaliser for York but was denied by goalkeeper Lance Cronin.

[14] On 17 September he joined Southern Football League Premier Division side Weymouth on non-contract terms,[15] before being released by the club on 7 October.

[16] On 19 November Pitt joined Conference North side AFC Telford United on non-contract terms after a successful trial with the club.

Former York City FC Manager Martin Foyle described Pitt as a player who "can take people on, is great at set-pieces and can provide an outlet on that left side".