After starting his career on his native island, he moved to Bournemouth as a 16-year-old and went on to become a regular in their first team, helping them avoid relegation from The Football League in 2009 and earn promotion a year later.

In November 2012 he was loaned back to Bournemouth, until making the deal permanent in January 2013, and contributed to them winning the Football League Championship title in 2015.

[4] 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.

[7] 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.

[10] Three days later it was reported by Sky Sports News that newly promoted Premier League side Blackpool had made a bid of £400,000, possibly rising to £600,000, to sign him.

The following day, it was reported that Bournemouth chairman Eddie Mitchell had blocked the bid and that the Seasiders had been prevented from opening talks with Pitman.

[17] Pitman did not score for the Robins until his 13th game on 20 November, when he came on at half time for Lee Johnson and opened a 2–0 win over Leicester City at Ashton Gate that moved his team out of the relegation zone.

[21][20] Four days after his return, he came on as a 73rd-minute substitute for Matt Tubbs away to Bury and scored an added-time equaliser to ensure a 2–2 draw at Gigg Lane.

[22] On 26 January 2013, he scored all of the Cherries' goals in their 3–1 home win over Crewe Alexandra, two of which were penalties, and was substituted so that he could receive a standing ovation.

[23] He finished the season with a streak of nine goals across eight consecutive games, concluding on 20 April with one in a 3–1 home win over Carlisle United that won promotion to the Championship.

[24] During the 2014–15 season Pitman helped Bournemouth win the Championship title and in doing so earn promotion to the Premier League for the first time in the club's 125-year history.

[26] He made his debut on 11 August in a home game against Stevenage in the first round of the League Cup, assisting Jay Tabb's winner in a 2–1 victory.

[27] Eleven days later he scored his first goal for the Tractor Boys, heading Freddie Sears' cross to open a 2–1 away win over Preston North End.

[47][48] Following his release from Bristol Rovers, Pitman joined Wessex League side AFC Portchester on a one-year deal, signing in a player/coach role.

[49] In January 2023, Pitman became the first player in the top nine tiers of English football to reach thirty goals, having scored thirty-six in all competitions.