Stonehouse, Lanarkshire born wing half Bobby Whitelaw began his football career with Larkhall Thistle in 1925 and headed south to join Third Division (North) Doncaster Rovers in July 1926, making his Football League debut at Wrexham the same October. He had four seasons at Belle Vue but was a fringe player throughout, scoring twice in 36 appearances before returning to Scotland to join Glasgow Celtic in August 1930. He made his Scottish League debut at Hamilton Academical that September, being used principally as deputy to Chic Geatons, and while at Celtic he had a loan spell with Albion Rovers late in 1930, before being released in June 1932, when he joined Bournemouth & Boscombe Athletic.
At Bournemouth he scored twice in 10 appearances during 1932-33 before heading over to Irish League football, joining Glentoran in 1933, also having brief spells with Coleraine and Linfield. Later the same year he returned to Scotland to join Queen of the South, from where he briefly rejoined Celtic, making the last of his 18 appearances for The Bhoys before joining Cowdenbeath in June 1934. After a loan spell at Hamilton Academical he moved to Albion Rovers in 1935, before returning to Ireland for another spell with Glentoran later that year.
In May 1936 he returned to the Football League, signing for Second Division Southampton, and he scored once in 20 appearances for The Saints as they flirted with relegation, eventually finishing in 19th place. He was not offered a new contract and finally joined non league Kidderminster Harriers in May 1937 before his eventual retirement.
NB in the photograph he is in the light suit with Southampton reserve team player Billy Moore.