James Gilmour was born on May 21, 1925, in Ayr, Scotland. He started his soccer career as a goalkeeper with local club Maybole. Jimmy served with the Scottish Command while doing army service.

After his army service Jimmy emigrated to Canada and joined Toronto St. Andrew’s. He won the British Consols Trophy, emblematic of being Toronto city championship, three times while with St. Andrew’s. In 1953 he was picked to represent the Ontario All-Stars in exhibition games against the Irish National team and against Liverpool Football Club.

After five years with St. Andrew’s he joined Sparta in the National Soccer League.After three years with Sparta he joined Ulster United.

Jimmy was Ulster United’s goalkeeper when they played against touring English First Division club Manchester City on June 8, 1958. The match played in front of 6,000 soccer fans at University of Detroit Stadium. Manchester City easily won by an 8-2 score. After one season with Ulster United he retired as a goalkeeper.

After his retirement Jimmy from professional soccer Jimmy became a coach. In 1961 he was an assistant coach with Toronto City in the Eastern Canada Professional Soccer League.