In the 1904–05 football season Gillespie was the team's fourth top scorer with 7 league goals in 16 games behind Sandy Turnbull who scored 19 goals and Billy Meredith and Frank Booth who both scored 8 goals. Manchester City finished third in the league that season, two points behind champions Newcastle United. At the end of the season the Football Association conducted an investigation into the financial activities of Manchester City and discovered that the team had been paying their players extra. The Football Association ruled that manager Tom Maley should be suspended from football for life while seventeen players were fined and suspended until January 1907. Gillespie refused to pay his fine and instead emigrated to the United States. In 218 games for City he had scored 128 goals.