[6] His younger twin brother, Dave Gillespie, also played for Carlton (90 games from 1906 to 1912, including the 1906 and 1907 premierships).

[11] Gillespie was discovered by Jack Worrall when the Carlton coach saw him kicking the ball with some friends at Princes Park.

Gillespie missed out on being part of Carlton's third successive premiership in 1908 due to injury.

Along with Alex Lang and Doug Fraser, Gillespie was dropped for the semifinal against South Melbourne while the club and league investigated the allegations that they had been paid to play poorly.

The full-back spent the 1911 football season with Brunswick in the VFA before returning to Carlton the following year, where he made his tenth finals appearance before retiring.