We present a case of a 55-year-old male with a history of urethroscopic calculus removal who later developed urinary tract infection (UTI), complicated by periurethral abscess formation with osteomyelitis of the inferior pubic ramus and a urethrocutaneous fistula after surgical drainage of the abscess. UTI with periurethral abscess and urethrocutaneous fistula (watering-can perineum) is a rare complication of UTI. A periurethral abscess with pubic osteomyelitis has not been previously reported.