Here, we report fossil leaves, woods, and pollen grains comparable to Calophyllum L. (mainly to Calophyllum inophyllum L. and Calophyllum polyanthum Wall. ex Choisy) of Calophyllaceae from the upper (Kimin Formation, late Pliocene-early Pleistocene), middle (Subansiri Formation, Pliocene) Siwalik sediments of the Arunachal sub-Himalaya, and lower (Gish Clay Formation of Sevok Group; middle to late Miocene) Siwalik sediments of the Darjeeling foothills, eastern Himalaya. Their presence indicates a warm and humid tropical environment in the region during the period of Siwalik sedimentation. Considering all records of Calophyllum, it is suggested that Calophyllum was a frequent forest element throughout the period of Siwalik sedimentation during the Neogene (Miocene time). At present, C. polyanthum grows in the eastern Himalaya, but C. inophyllum is totally absent from north-eastern regions suggesting differential adaptability of these taxa to changing ecoclimatic conditions. Distinct climate change in the area, possibly related to the Himalayan Orogeny during Miocene–Pleistocene times, might have caused the disappearance of C. inophyllum from the entire eastern Himalaya and north-east Indian plains and a move to littoral/coastal and swampy forests of India and other adjoining south-east Asian regions, Polynesia, and the east coast of Africa. The past global distribution of Calophyllum is also discussed, and it is suggested that India may have been its primary centre of origin. This is the first time Cenozoic fossil leaves Calophyllum siwalikum Khan, R.A.Spicer & Bera, sp. nov. comparable to C. inophyllum are described using the both macro- and micromorphological characters. © 2017, Springer-Verlag Wien.