Harold Maskiell was born in Melbourne in 1892 and like many families at that time moved to Western Australia in the mid 1900s. He would have learned his football school and by 1909 was making appearance for Claremont’s junior teams. By 1915 he featured regularly in their senior team.
He enlisted at the start of 1916 as a Sapper in the 1st Tunnelling Company. His wartime service was interrupted when he fractured his right fibula playing football in France on 30 July 1917. The injury necessitated his transfer to England for his recovery. By April 1918 he was back in the field in France until the end of the war.
Upon his return he turned out for Claremont in 1920 and 1921 season. On 14 January 1922 Harold Maskiell married Josephine Evert and pulled up his boots to concentrate on having a family, his son being born nine months later.
After the death of his wife, and service in World War 2, he move back to Victoria and passed away in Collingwood in 1957 at the age of 65.