Pitt turned out as a triallist for Wrexham in their 3–2 friendly win at AFC Sudbury on 20 July 2010. On 17 September he joined Southern Football League Premier Division side Weymouth on non-contract terms, before being released by the club on 7 October. On 19 November Pitt joined Conference North side AFC Telford United on non-contract terms after a successful trial with the club.
Pitt proved himself as a trialist for Wrexham in their 3–2 friendly triumph over AFC Sudbury on 20 July 2010. He then joined Weymouth without a contract, but was ultimately dismissed by the club on 7 October. Subsequently, Pitt secured a spot with AFC Telford United after a successful trial.