He studied for the Indian civil service, and having been admitted as a probationer went on to Merton College, University of Oxford, England.
In 1875 Cuthbertson joined the staff of the Geelong Grammar School as classical master under the pretense that he had completed his degree at Oxford.
He had enjoyed a close relationship with the students of the school and the former Head Master, John Bracebridge Wilson, however, his alcoholism was well known and boys were placed on "Cuthy duty", which involved at times pulling him out of the gutter.
After a visit to England he lived for a period at Geelong and then near Melbourne, still occasionally sending verse to the school magazine.
He died suddenly from an overdose of veronal while staying with a friend at Mount Gambier on 18 January 1910.