Gilmore was recruited from Koondrook, a town on the Victorian side of the Murray River.
[3][4] He made 11 league appearances in his time at Essendon, never more than four in a single season and was a member of the club's 1950 and 1952 seconds premierships.
[3][4] In 1954, Gilmore joined Richmond, where he played briefly in the seconds, before leaving for Kyneton.
[5][6] He spent the 1955 VFL season with St Kilda and put together 10 games that year, all in succession, a run which ended when he was forced to sit out four weeks for striking Carlton's Noel O'Brien.
[4][7] Also a professional runner, Gilmore competed in the Stawell Gift and once won the quarter mile race.