Bobby Gillespie was born in 1900 in Strathbungo in touching-distance of Queen's Park itself and almost of all three Hampden Parks. His father a locally-born Clothier, the manager of a tailoring company, and his mother English, whose maiden-name was also English. He began his football at Battlefield in neighbouring Langside, at eighteen stepped up and made his debut for The Spiders and from nineteen was a regular in the first team as a centre-half, who could also play up-front. 

However, the first couple of years of his senior career were not as smooth as they might have been. In 1920 Queen's Park finished fourteenth of twenty-two in the only division. In 1921 it was nineteenth but in 1922 found itself relegated to the newly-created Second Division. However, the club did bounce straight back up, first to survive and then move into no more than mid-table safety. 

It was a record that was far from stellar and therefore it is perhaps not surprising that Gillespie's qualities took a little time to be appreciated fully. But when they were it is was in an initial rush. He was award both his first amateur and "full" caps in the same year, 1926, he aged twenty-five, and continued to add to the former over the next seasons. However, the latter had been as a late replacement and for a while he had to wait. Yet the opportunity did come and in 1930 by when, aged twenty-nine and with four hundred club starts he had proved himself, the national captaincy from now on, an amateur in an otherwise professional eleven, a recognition. 

And it was that same year, 1930, that his personal circumstances changed. He married, his wife Annie Anderson from Glasgow. They were to have three children, two boys and a girl, of whom two survived, and settle in the centre of Old Cathcart village, where in 1960 Bob was to pass away at the age of just fifty-nine.