Dematiaceous fungi are defined by pigment within their cell walls. They are increasingly recognised human pathogens, causing a wide range of clinical presentations, from localised subcutaneous infections to disseminated disease in rare cases. We report our institutional experience with diagnosis of dematiaceous fungal infections from 2005 to 2022 and highlight four instructive cases that clinically and pathologically mimicked other diseases for which the diagnosis was confirmed by fungal culture (one case) or supported by PCR with 28S rRNA and internal transcribed spacer primers (three cases). Two patients were immunocompromised and two had presumed exposure to the organism. In each highlighted case, fungal infection was not clinically suspected, and the pathologist was critical in making the diagnosis and ensuring appropriate clinical management, which was supplemented by fungal stains and novel molecular methods.