Abstract Dematiaceous fungi have a diverse clinical spectrum that presents a difficult problem in diagnosis and treatment. These opportunistic pathogens are of concern in healthy, debilitated, or immunocompromised individuals. We describe three patients with localized cutaneous infections produced by dematiaceous filamentous fungal organisms with varying clinical presentations. Two patients were immunocompromised, and a third was otherwise healthy. The unusual clinical and unique histologic features of these difficult infections are reported in detail, as is their successful medical management with ketoconazole (Nizoral) and an experimental antifungal agent, fluconazole.