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Richard Olaf Winstedt was born in Oxford and graduated from New College, Oxford. In 1902 he became a cadet in the Federated Malay States Civil Service, and was posted to Perak where he studied Malay language and culture. In 1913 he was appointed District Officer in Kuala Pilah, and in 1916 appointed to the Education Department. In 1920 he received his DLitt degree from Oxford. He served as the first President of Raffles College, Singapore, 1928–1931. During his presidency, he also served as acting Secretary to the High Commissioner, 1923, Director of Education for Straits Settlements and Federated Malay States (FMS), as a member of Legislative Council, Straits Settlements, 1924–1931 and as a member of the FMS Federal Council, 1927–1931. He was president of the Malayan Branch of the Royal Asiatic Society in 1927, 1929 and 1931. After a term as General Adviser to Johore, 1931–1935, Winstedt retired from the Malayan Civil Service.

He returned to England and was appointed Lecturer, then Reader, and ultimately Honorary Fellow, in Malay, at the School of Oriental Studies in London, where he also served as a member of the Governing Body, 1939–1959. During World War II, he broadcast in Malay to Japanese-occupied Malaya. He retired from active teaching in 1946.