We report a case of penicilliosis in a Filipino man with HIV-AIDS who presented with skin-colored and erythematous to hyperpigmented, umbilicated papules and nodules on the face, trunk, and extremities associated with fever, lymphadenopathy, and anemia. The diagnosis was made through skin biopsy and fungal culture, which showed characteristic paintbrush-like hyphae and conidiophores. The patient was treated with intravenous amphotericin B at 0.6 mg/kg/day for 14 days followed by oral itraconazole 200 mg twice daily for 10 weeks resulting to flattening of lesions with hyperpigmentation, and prevention of appearance of new lesions. Resolution of fever, lymphadenopathy and improvement of anemia were also noted. He was placed on maintenance regimen with itraconazole 200 mg once daily to prevent relapse. Early diagnosis and appropriate management is important because mortality of disseminated disease is high if diagnosis and treatment are delayed.