<p>Phaeohyphomycosis is a rare opportunistic infection caused by dematiaceous or pigmented fungi. While typically localized to the extremities, involvement of the head and neck is extremely rare and often clinically indistinguishable from neoplastic or chronic granulomatous diseases rampant in Indian settings. Melanin in the fungal cell walls serves as a defining characteristic and a primary virulence factor. This report aims to describe the clinical features, diagnostic challenges, and management strategies in a series of patients presenting with head and neck phaeohyphomycosis at a tertiary care centre in India. A retrospective analysis was conducted on three patients with atypical facial swellings. Evaluations included clinical history, high-resolution imaging, and histopathological assessment using special stains (PAS, GMS, and Fontana-Masson). Management involved surgical debridement combined with systemic triazole therapy. Presentations ranged from indolent premaxillary masses to aggressive sinonasal lesions with periorbital extension and bone erosion. Initial assessments favoured malignancy in two cases due to significant bony erosion. Histopathology confirmed brown-pigmented, septate hyphae in all cases. Complete surgical clearance followed by a twelve-week course of oral itraconazole resulted in a complete resolution of disease with no signs recurrence at follow-up. Head and neck phaeohyphomycosis is a clinical “masquerade” that must be considered in the differential diagnosis of atypical facial &amp; sinonasal masses. Synergistic therapy comprising of both surgical debridement and triazole therapy leads to excellent outcomes.</p>