In the 1901–02 football season Gillespie was the team's top scorer with 15 goals in 24 games. However, City finished in 18th place with only 28 points and were consigned to division two once more. As a consequence, Sam Ormerod resigned as Manchester City manager and was succeeded by Tom Maley. Maley strengthened the team by purchasing Billy Lot Jones, Sandy Turnbull and Jimmy Bannister and they immediately earned promotion back into the first division in the 1902–03 football season by winning the Second Division championship. The team scored 95 goals in 34 games that season and Gillespie was the Second Division's top scorer with 30 goals.