After being severely injured in World War I, he was repatriated to Australia and, later, died of his wounds.
[4][5][6][7] His younger twin brother, Doug Gillespie, also played for Carlton (90 games from 1906 to 1912, including the 1906 and 1907 premierships).
[15] His second last match for Brunswick was against Port Melbourne on 22 May 1915, when he was badly injured; and, at the time, it was supposed that he would not play again in that season.
[16] He did return, however, and played his last match (at full-back) in the VFA Grand Final against North Melbourne on 7 August 1915 – when he was brought from his Army training camp to play for Brunswick in place of ex-Coburg footballer Robert Leslie "Les" Broom (1892-1915), who had been playing at full-back in Gillespie's stead once Gillespie had enlisted in July 1915.
He was wounded, in action, when hit in the spine by shrapnel at Armentières in France on 19 July 1916.