The genus Diospyros (Ebenaceae) is highly diverse throughout Malesia, and New Guinea is thought to host c.46  species. Here we present a taxonomic treatment of a group of vegetatively similar species from the region, characterised by the large, chartaceous leaves that develop a peculiarly dark colour when dried. As a result of examination of herbarium collections, we describe two species new to science, Diospyros multimaculata and D. tehno; we exclude the presence of D. rostrata from New Guinea; and we provide a key to these and the three other species with a similar habit, namely, D. janowskyi, D. fusicarpa and D. pulchra.