 In the 1903–04 season, Gillespie was City's top league goalscorer with 18 goals as the team finished in second place in the First Division, three points behind champions Sheffield Wednesday.City had defeated Sheffield Wednesday 3–0 in the semi final of that seasons FA Cup, with a brace from Sandy Turnbull and one goal from Gillespie.City played Bolton Wanderers and won 1–0.