T. W. Rolleston graduated from Trinity College, Dublin in 1878 and was editor of the Dublin University Review from May 1885 to December 1885. He was friends with W. B. Yeats and helped found the Irish Literary Society in London in 1892. Rolleston was a journalist who wrote for the Irish press and then moved to Hampstead, North London, in 1909. He was a regular contributor to The Times Literary Supplement, specialising in Oriental subjects.
In 1910, Rolleston was involved in the foundation of the India Society. He acted as Treasurer and then Honorary Secretary of the Society. Rolleston was involved in the aim of establishing a Lectureship in Indian Art at the School of Oriental Studies, but was unsuccessful in raising enough funds before his death in 1920.
Harihar Das called Rolleston 'a friend of India' and praised him for 'his service to Indian culture' in an obituary written for The Asiatic Review in January 1922.