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To describe a rare case of gummatous syphilis of the penis with urethrocutaneous fistula mimicking penile carcinoma causing a diagnostic dilemma. A 54 year old man presented with an ulcerative lesion on glans penis. Patient was managed with partial penectomy in view of erosive growth giving rise to urethrocutaneous fistula. Histopathology showed granulation tissue, necrotizing vasculitis and epithelioid cell granuloma. Immunohistochemistry stained positive for Treponema and patient was treated accordingly. Syphilis is rarely encountered i