Born in Millicent, South Australia, Cumming moved to Western Australia with his family at an early age. He made his senior debut for the Perth Football Club in the West Australian Football League (WAFL) at the age of 15, while still a high school student. In 1911, Cumming moved to Melbourne to attend the University of Melbourne, playing two seasons for the University Football Club in the Victorian Football League (VFL). He then returned to Perth and played one final WAFL season in 1914. Cumming enlisted in the Australian Imperial Force the same year, and served in the Gallipoli Campaign and on the Western Front. He was awarded the Military Cross in 1917, and received a bar the following year. He died of wounds after the Second Battle of Villers-Bretonneux.