He later joined the colonial secretariat and became the personal assistant to the Director of Education of the Straits Settlements, working for many years under Richard Olaf Winstedt.
[2] During the Japanese Occupation of Singapore, Dorai Raj served as the personal assistant to Captain Andrew Tokuji Ogawa, who had been appointed the Director of Education.
After successfully obtaining permission from Ogawa, Dorai Raj spent four days transferring the books to the Fullerton Building, which had been converted into the new headquarters for the Education Department by the Japanese.
On 26 August 1945, following the end of the occupation and as he was about to return to Singapore, he received word that the books had been transferred to Taiping, Perak, where they were to be distributed to teachers and others there by Japanese officers.
Dorai Raj then left for Taiping with an interpreter and was successful in persuading the officers not to distribute the books, and to instead relocate them to the local convent until they were claimed by either Raffles College or the Education Department.