James's birth had been in 1868, one of seven children. His parents had both come to Glasgow from Beith, his father working as a Leather Currier and Salesman. And having started work as a Message Boy young Jimmy was also playing for the Glasgow Green, junior team, Star, formed in 1886, dissolved in 1889, as in 1888 it reached and lost the final of the Glasgow Junior Cup. And it was following that game and at the age of twenty that he, a strongly-built. rapid right-winger with a fierce shot, was signed to Clyde, then playing just up the river at Barrowfield Park in Dalmarnock. 

Clyde would not be one of the clubs to form the Scottish League in 1890. It would only join in 1891, replacing Cowlairs. But by then, after three seasons with the Bully Wee Jimmy had made a decision to try his hand elsewhere, heading to Sunderland, where one of its teams was in the Football League and about to be champion and the other was not, but since its formation in 1888 and whilst only in the Northern League had nevertheless recruited heavily North of the Border. He first joined the latter, it giving him work and training as a cabinet-maker and upholsterer, but spent little more than a season there before it folded. But in the meantime he had clearly made something of an impression north of the river because the former then took him on, albeit as a reserve, but one who within months was in a first team as it repeated the title-win, and by some distance. 

Gillespie was to remain at Newcastle Road, Sunderland's pre-Roker ground, for five seasons, as the club under Tom Watson took a third title in 1895, having in 1894 been runner-up. But, as his team "tumbled" to sixth, Watson was to leave at the end of the 1895-6 season, replaced by Robert Campbell, the team then stuttered and badly and in 1897 Jimmy was on his way. On the face of it and at the age of twenty-nine it looked as if he was perhaps surplus to requirements but in fact there was a much more obvious reason. In 1896 back in Glasgow in Blythswood he had married Margaret Howe. She had come to Wearside, their first child was born there in 1897, but there was clearly a desire to return home, where the football abilities of her husband would prove to be both in demand and recognised. He joined Third Lanark, was early in 1898 in the Scottish League team and then capped against a Wales, where he scored a hat-trick.

However, the cap was won just three days before Jimmy Gillespie's thirtieth birthday and time was catching up with him. Although he he did not fully retire until 1903 he from 1899 played sparingly, until 1902 at Thirds and for a final season at Ayr. Meantime, he first worked in The Gorbals at his Sunderland-learned trade, eventually moving to, settling and setting up his own upholstery-business in Hillfoot in Bearsden. And it was there that he was staying in 1932 when he died at sixty-four in hospital in Glasgow, a widower, Margaret having passed away eight years earlier again in the city at the age of just fifty-three.