Dumbarton, Dunbartonshire born inside right Jimmy Stewart began his football career with Glasgow Ashfield and first played senior Scottish League football after signing for Motherwell in 1906, where he scored 26 goals in 72 appearances before being signed by First Division club Liverpool in April 1909, making his Football League debut at Chelsea the same September. Missing only one match in his debut season, Stewart scored 18 goals as The Reds finished runners up in the League Championship, being only outscored by Jack Parkinson. His total included a hat-trick in a win over Chelsea in the return match at Anfield in January 1910.
That debut campaign was easily Stewart’s best in a Liverpool shirt. He was only called on a further 25 times over the next four seasons and made the last of his 63 League and FA Cup appearances for the club in a 4-1 defeat at Sheffield Wednesday on 4th October 1913, scoring 26 goals for Liverpool. He returned north to join Hamilton Academical towards the end of 1913, In 1916 he had a spell with Dumbarton before returning to The Accies in 1918, where he saw out his playing career.
After retirement Stewart was trainer at Blackpool for a long spell before being appointed at Dundee where he stayed only one season, and he then moved to the south coast to train the players of Portsmouth in 1937.