Pittman began his career at Hamilton Academical and on 25 March 2011, he signed on loan for Alloa Athletic.[2] He was first called up for a matchday squad on 26 March 2011, remaining an unused substitute for their goalless home draw with Peterhead in the Scottish Second Division.[3] Three days later, he made his only appearance for the club, as a last-minute substitute for Jim Lister in a 3–2 defeat at Brechin City.[4]
On 11 August 2011, having been released by Hamilton,[5] Pittman signed for junior club Broxburn Athletic, managed by his father.[1] He later continued his junior career with Bo'ness United joining the club in June 2014.[6]
On 7 May 2018, in the first leg of the Scottish Premiership play-off semi-final, Pittman scored the winning goal as Livingston won 3–2 away to Dundee United.[11] He scored again in the first leg of the final, getting Livingston's second goal in a 2–1 win at home against Partick Thistle.[12] He also played in the second leg as Livingston won 1–0 to complete a 3–1 aggregate victory to gain promotion to the Scottish Premiership.[13]
On 22 March 2019, Pittman signed a new contract, keeping him at Livingston until 2021.[14]
During his spell at Livingston, Pittman has broken several records. In April 2022 he became the club's record top-flight appearance holder with 124, surpassing Oscar Rubio's tally.[15] In August the same year he became the record appearance holder in the Livingston era, breaking Keaghan Jacobs' record.[16]
In October 2022 Pittman signed a further contract extension, penning a three-year deal lasting until the end of the 2025/26 season and taking him into a testimonial year.[17]
Career statistics
As of match played 24 September 2024
Appearances and goals by club, season and competition