Zinner syndrome is a rare condition comprising a triad of unilateral renal agenesis, ipsilateral seminal vesicle obstruction and ipsilateral ejaculatory duct obstruction. The mutual embryological origins of the seminal vesicle and the ureteral bud result in both anomalous genital and urinary tracts. We present the case of a 39-year-old patient where the initial presentation of this condition was bladder outflow obstruction. In this paper, we discuss the embryological origin of this condition, the range of imaging tools used to diagnose Zinner syndrome and the inherent benefits and shortcomings of each modality.