Primary urothelial carcinoma of the prostate is a rare clinicopathological entity which as a rule bears an unfavourable prognosis. We report a case of a 75 year old male who presented with a history of voiding difficulty. With a provisional diagnosis of Benign Prostate Hyperplasia both clinically and by needle biopsy a Trans Urethral Resection was undertaken. Histopathology showed acini lined by malignant transitional epithelial cells with stromal invasion. No primary in the bladder was detected on the investigation. A CK 7/ CK 20 copositivity on Immunohistochemistry confirmed our diagnosis of Primary Urothelial Carcinoma of Prostate.