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The distribution of calcareous dinoflagellates has been analysed for the Maastrichtian–Miocene interval of Ocean Drilling Project Hole 689B (Maud Rise, Weddell Sea). The investigation thus represents a primary evaluation of the long-term evolution in high-latitude calcareous dinoflagellate assemblages during the transition from a relatively warm Late Cretaceous to a cold Neogene climate. Major assemblage changes during this interval occurred in characteristic steps: (1) an increase in relative abundance of tangentially structured species – particularly Operculodinella operculata – at the Cretaceous/Tertiary boundary; (2) a diversity decrease and several first and last appearances across the Middle–Late Eocene boundary, possibly attributed to increased climate cooling; (3) a diversity decrease associated with the dominance of Calciodinellum levantinum in the late Early Oligocene; (4) the reappearance and dominance of Pirumella edgarii in the Early Miocene, probably reflecting a warming trend; (5) monogeneric assemblages dominated by Caracomia spp. denoting strong Middle Miocene cooling. The results not only extend the biogeographic ranges of many taxa into the Antarctic region, but also indicate that the evolution of high-latitude calcareous dinoflagellate assemblages parallels the changing environmental conditions in the course of the Cenozoic climate transition. Therefore, calcareous dinoflagellates contribute to our understanding of the biotic effects associated with palaeoenvironmental changes and might possess the potential for reconstructing past conditions. The flora in the core includes one new taxon: Caracomia arctica forma spinosa Hildebrand-Habel and Streng, forma nov. Additionally, two new combinations are proposed: Fuettererella deflandrei (Kamptner, 1956) Hildebrand-Habel and Streng, comb. nov. and Fuettererella flora (Fütterer, 1990) Hildebrand-Habel and Streng, comb. nov.