Jimmy played for Scottish clubs East Stirlingshire, Dundee, Falkirk and Rangers, before moving to England to sign for Preston North End and later the now dissolved Leyton.

In May 1907 he was bought by Manchester United, where he won the 1907–08 Football League title, the 1908 FA Charity Shield and the 1908–09 FA Cup. He scored a total of 45 goals in 78 games for the club, with his best season being 1908–09, in which he scored 22 times in 28 appearances in all competitions. He was sold to Bradford Park Avenue in September 1910.

An inside or centre-forward he signed for Chelsea during the summer of 1912 and stayed at Stamford Bridge for just over a year.

Jimmy played in the annual Home Scots v Anglo-Scots international trial match in 1911, but did not receive any other representative honours.

Jimmy played for Scottish clubs East Stirlingshire, Dundee, Falkirk and Rangers, before moving to England to sign for Preston North End and later the now dissolved Leyton.

In May 1907 he was bought by Manchester United, where he won the 1907–08 Football League title, the 1908 FA Charity Shield and the 1908–09 FA Cup. He scored a total of 45 goals in 78 games for the club, with his best season being 1908–09, in which he scored 22 times in 28 appearances in all competitions. He was sold to Bradford Park Avenue in September 1910.

An inside or centre-forward he signed for Chelsea during the summer of 1912 and stayed at Stamford Bridge for just over a year.

Jimmy played in the annual Home Scots v Anglo-Scots international trial match in 1911, but did not receive any other representative honours.