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 was tested out for Wrexham in their 3–2 friendly win against AFC Sudbury on 20 July 2010. He then joined Weymouth, a Southern Football League Premier Division club, without a contract, but was released by them just two weeks later. Finally, Pitt signed with AFC Telford United, another Conference North team, after impressing in a trial.