[3] In 1906 he entered the Indian Civil Service, education branch,[4] and became Principal of Government Arts College, Rajahmundry from 1909.

Historian Digavalli Venkata Siva Rao (1898–1992), who studied in Rajahmundry between 1910 and 1916, wrote about him in Telugu, as did Couldrey's friend and favourite student, Adivi Bapiraju, and a few others.

He dedicated his book South Indian Hours, which was published in England in 1924, to his three favourite students: Adivi Bapiraju, Kavikondala Venkatarao and Damarla Venkata Ramarao.

In that book he paid rich tributes to Telugu language "our Indian neighbours conscious of vague but proud tradition of ancient empire prefer to speak of Andhra Country.

He was also a great sportsman and encouraged his students to take part in many kinds of manly sports such as horse riding, swimming, excursions, mountaineering, cricket, football, Hockey and tennis.

Oswald Couldrey liked music, poetry, painting and fine arts and was himself a musician, poet and painter.

Couldrey gladly attended these dramas to make friends with the actors and Mr. A.S. Ram, the artist who used to draw scenery on the screen.

After he returned to England in 1920, Couldrey wrote to one of his erstwhile students about meeting his ex-colleague, S. Radhakrishnan in Oxford in 1927.