Dunbartonshire born outside right James Gillespie joined Football League club Sunderland in the summer of 1890 after spells in Scotland with Renton in 1888 and Greenock Morton in 1889, making his Football League debut against Wolverhampton Wanderers that September, scoring twice in a 3-4 home defeat. After just one more match for Sunderland, he moved to their Football Alliance rivals Sunderland Albion later in 1890, but returned to Roker Park in 1892 when Albion disbanded. An integral member of “The Team of All Talents”, Gillespie won the Football League Championship twice with Sunderland, in 1893 and 1895, scoring 12 and 14 goals respectively during those campaigns, and won the 1895 “World Championship” when Sunderland won 5-3 against Heart of Midlothian (the Champions of Scotland) at Tynecastle. He scored a total of 54 goals in 147 appearances in all competitions for Sunderland.
He returned to Scotland in 1897 with Third Lanark and it was with the Glasgow club that he won his only Scotland cap. Despite scoring a hat-trick in Scotland’s 5-2 win over Wales at Fir Park, Motherwell on 19th March 1898 (with the other two goals from fellow-debutante, James McKie), he was never capped again for his country, although he had also represented The Scottish League in January 1898 when they beat The Irish League 5-0, with Gillespie scoring one of the goals. Having scored 10 goals in 32 appearances for The Warriors, he joined Ayr United in 1898, scoring 7 goals in 17 appearances for The Honest Men, his last known club before his eventual retirement.