Pitt began his career with
Premier League club
Chelsea, progressing through the youth ranks at
Stamford Bridge. Pitt joined
First Division side
Portsmouth on a three-year contract on 16 June 2001 when his former Chelsea coach
Graham Rix took over as manager at
Fratton Park, turning down the offer of a new three-year contract at Chelsea. and he finished his first season with the club,
2001–02, with 41 appearances and three goals. He came on as a substitute on 73 minutes in the
2010 Conference National play-off final at
Wembley Stadium on 16 May, which was lost 3–1 to Oxford. 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. He stayed with the club until January 2012 when he left by mutual consent. On 25 February, Courtney made his debut for
Chasetown against
Stocksbridge Park Steels in the
Northern Premier League Premier Division. He joined
Stafford Rangers in July 2012 ahead of the 2012–13 season. On 25 October Pitt left Stafford Rangers by mutual consent. ==Style of play==