Robert Wilson was educated at the newly founded Bradfield and Cheltenham Colleges, and won a Postmastership at Merton College. He was a Fellow of Merton College, Oxford, and first appointed as a Fellow of Radley College from 1863 to 1866, under the Wardenship of Richard Norman. He left Radley to serve as an assistant master at Marlborough College from 1867 to 1869. He then returned to Merton College as a Tutor from 1870 to 1875, and as Vicar of Wolvercote, 1875-1879. After leaving Radley, he became Warden of Keble College, Oxford, from 1888 to 1897.

He is remembered as one of the most able of Radley’s early Wardens, and credited with its survival after it faced failure in 1878.

In addition to supporting the activities of the Natural History Society, Wilson was instrumental in re-introducing and promoting the Shakespeare Society, an initiative of Richard Norman in the 1860s. This later became the Literary Society.