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A 26-year-old unmarried male presented with voiding difficulty and penile oedema, was initially diagnosed and treated for Mondor’s disease, which is a rare, benign, usually self-limiting pathology of anonymous origin. When he failed to respond to conservative management, a biopsy from glans penis was taken which revealed it to be moderately differentiated Squamous Cell Carcinoma (SCC). Apart from being an old man’s affliction, usual presentations of penile cancer range from ulcerative lesion to exophytic growth. Thus, its presentation as thrombosis of dorsal vein of penis is astounding as depicted in this case.