The ureter is a subject to a number of natural variations, and duplex ureter is one of the rare congenital abnormalities affecting the ureter, occurring in around 1% of general population1. We here are reporting a case of a 25 year old gentleman, who had come with complaints of pain on the left flank and LUTS (Lower urinary tract symptoms). Investigations revealed that he had ahydronephrotic left kidney, with the upper pole showing pyonephrosis with suboptimal function. This was associated with a unilateral duplex moiety with complete duplication of ureters on the left side and ectopic insertion of the upper moiety ureter into prostatic urethra. The lower moiety collecting system was hydronephrotic but non obstructing and non refluxing. The patient subsequently underwent aleft sided partial upper pole nephrectomy. Most cases of duplex ureters present in childhood and adolescence, and are usually asymptomatic. This case report emphasizes the need to consider the possibility of such anomalies and their varied spectrum of presentation and the need for screening of such anomalies at an earlier stage.