Pitman scored seven goals during the 2007–08 season, but was unable to prevent Bournemouth from being relegated to League Two. The following season, he was sent off just three minutes after he came on as a substitute in Bournemouth's FA Cup second round exit against non-league side Blyth Spartans. On 4 April 2009, he scored a hat-trick in a 4–0 home win over promotion-chasing Rochdale as Howe's Bournemouth gained points to retain their place in The Football League. He totalled 26 goals in 2009–10 as the Cherries won promotion back to League One, including one on 1 May 2010 as they sealed their promotion with a game remaining by defeating Port Vale 4–0.