He is a son of Steve Pittman, who played for Dundee, East Fife and Partick Thistle as a full back, and also represented the United States at international level.
[7] Four days after his acquisition, he made his debut in a 3–2 home defeat to Heart of Midlothian, playing the final four minutes in place of Ibra Sekajja.
[8] On 5 April, Pittman played the full 90 minutes of the 2015 Scottish Challenge Cup Final at McDiarmid Park in Perth, scoring the first goal of a 4–0 win over his former team Alloa.
[10] 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.
[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.