An English bulldog was referred to the Veterinary Medical Teaching Hospital-University of Wisconsin (VMTH-UW) for re-evaluation of an 8-year history of chronic, recurrent prostatitis and cystitis. The patient was first referred to the VMTH-UW at 11 months of age with a history of antibiotic-responsive hematuria and stranguria. Four urinary tract contrast studies were performed during the 8-year time span; however, a rectourethral fistula was not diagnosed until the fourth study. The article presents a literature review of rectourethral fistula, describes the case management of the dog in this study, and provides an explanation as to the potential reasons the fistula was not diagnosed on the three previous imaging studies.