Glenboig, Lanarkshire born centre half Bob McSkimming began his football career with junior club Douglas Park in 1907 before joining Scottish League Albion Rovers in 1908. He impressed enough during his time at Meadow Park for First Division Sheffield Wednesday to step in for his signature, and he made his Football League debut against Tottenham Hotspur in March 1910, soon establishing himself as a first team regular for The Owls. His spell at Hillsborough was however brought to a halt by the suspension of peacetime football in 1915 due to the onset of the First World War.
During the War he played for Wishaw Thistle and joined Motherwell in 1915. scoring 3 goals in 90 appearances for The Steelmen during the four wartime seasons, before returning to Hillsborough in 1919 once the conflict had ended. He made 18 more appearances for Wednesday during 1919-20, taking his total for the club to 195, during which time he never scored, before returning to Albion Rovers in the summer of 1920, soon after they had been the beaten Scottish Cup Finalists. In 1923 he briefly joined Ayr United before joining Scottish League Third Division club Helensburgh later the same year, subsequently playing for Auchinstarry and Denny Hibernian in 1924 before retirement.