Rupert Roopnaraine was a lower order batsman and off-spinner who played cricket for Demerara county in Guyana and the Cambridge University in England. In 1954 he won a scholarship to Queen's College, where he excelled in cricket and was captain of the school team. He may have represented Demerara in inter-county competition while still at Queen's College.
In 1962 he was awarded a Guyana scholarship to attend Cambridge University in England, where he studied Modern Languages. He played first-class cricket for Cambridge University from 1964 to 1966 and was awarded a Blue for representing the university in the annual match against Oxford University in 1965 and 1966.
In 1970 he was awarded a scholarship to Cornell University, in New York, where he obtained an MA and PhD in Comparative Literature. From 1976 to 1996 he was a university lecturer in the UK, Canada, the US and at the University of Guyana. He joined the Working People's Alliance in 1977 and became a member of the Guyana parliament.