James H. Woolston obtained the degree Master of Arts (MA) at the University of Cambridge, England. He probably arrived in the Orange River Colony (now the Free State) in 1903, when he became a member of the recently founded Philosophical Society of the Orange River Colony. (This society resolved itself into the Orange Free State branch of the South African Association for the Advancement of Science in 1914). In January 1904 he assumed duty as the first professor of mathematics and applied mathematics at Grey University College in Bloemfontein, a post he held until 1911. The college, initially the advanced section of the Grey College School, became independent in 1904 and introduced teaching at the second and third year level of the BA degree. Shortly before the formation of the Union of South Africa in 1910 the college was formally recognised by legislation as a university institution.
Woolston represented the Orange River Colony on the council of the University of the Cape of Good Hope (an examining body only, and the only university in southern Africa at that time) from 1913 to 1918. In 1909 the university admitted him to the MA degree on the basis of his Cambridge qualification. By 1910 he was a member of the South African Association for the Advancement of Science. He was on active duty during World War 1 (1914-1918) and died of his wounds in 1918.