Pitman made his professional debut on 24 August 2005 in the second round of the Football League Cup, as a 114th-minute substitute for Stephen Cooke in a goalless draw away to Torquay United. Bournemouth won 4–3 on penalties. Three days later, he played his first league game, replacing Dani Rodrigues for the final two minutes of a 2–1 away win over Bradford City in League One. On 18 October, he scored his first goal for the Cherries in the Football League Trophy, a penalty to open a 4–1 win over Aldershot Town at Dean Court, and his sole league goal of 19 games that season was scored on 18 February 2006, in the fourth minute of a 1–1 home draw with Blackpool.