Gilmore started racing in November 1955 at the age of 10. He came second in his first race, a 1-mile event at York Park Track Launceston. Gilmore was awarded Australian Cyclist of the Year 1972.
Gilmore was a successful track rider on the European Six-day racing scene.
He won his second race, the same month, again a 1-mile event at York Park Track. He won several juvenile and junior championships before beginning to compete for prize money at the age of 15, which in Australian at that time deemed him a professional. In the same year he won the Australian national road race title.
In 1967 Gilmore was awarded both Australian Professional Road & Track Cyclist of the Year from "Road & Track" magazine readers, and became an inaugural member of the Tasmanian Sporting Hall of Fame.
