Alexander Winning was born on 17 September 1892 in Tsarist Russsia, in Kharkoff, which is now Kharkiv, Ukraine. He arrived in Albany with his mother from Scotland in June 1912. By 1913 he had moved to Perth and joined the Austral team, who he represented until the end of the 1915 season. The team disbanded in 1916 as they did not have numbers due to the war, so Winning played for a Perth Combined team during the 1916 season.
Private Winning came through his wartime service on the Western Front relatively unscathed. He was discharged from the AIF in June 1920 to continue studies in architecture in Scotland. Later in life he developed a considerable reputation as an architect.Â
He returned to Australia in 1921, married Dorothy Major in Coolgardie in 1923, and had three children with her. He died in March 1963 at the age of 70.