Sir Richard Olaf Winstedt has been widely regarded by scholars of Malaysia and Singapore as the last and greatest British scholar-administrator of colonial Malaya. He wrote more on the history, culture and language of Malaya than other British colonial writers of the region. Even today, no scholars could match his literary output. He remains influential in the region’s historiography and in the field of Malay studies, in spite of the criticisms that have been levelled on his works over the years and the attempts to revise and re-write history in the post-colonial period. This research analyses Winstedt’s position as a colonial scholar in Malaya during the colonial and post-colonial period. It discusses how he contributed to the colonial understanding of the region’s history, how his works were used by the colonial administration for crucial decisions and in debates concerning the future of Malaya, and how his works were regarded locally and by his Western contemporaries during the colonial and post-colonial period. Winstedt and his writings represent the continued influence of colonial knowledge in defining the past of many countries. This research is part of a larger intellectual history project on Winstedt’s writings and his contributions to Malaysia and Singapore’s historiography.