Urethral duplication is one of the rarest congenital urinary tract anomalies, commonly seen in association with hypospadias. The etiology of urethral duplication is not known and the embryological basis of the deformity is not clear. The most important point in the treatment plan is the determination of the functional urethra. Unless the surgeon suspects a duplication or an abnormal condition associated with the hypospadias a preoperative radiological examination should be omitted in most cases, which could lead to difficulties in surgical planning. In most cases the hypospadiac urethra is the functional one; therefore, this hypospadiac urethra should be preserved and the hypoplastic urethra should be excised. Voiding cystourethrography or retrograde urethrography could be very useful in determining the functional urethra if performed preoperatively. We report four patients with urethral misalignment and discuss the preferred surgical treatments. Three of the cases were frontal urethral duplication and the other was collateral urethral duplication, which was, to the best of our knowledge, the 10th case reported in the literature. Although the etiology is not clear, and the exact embryology of the malformation has yet to be defined, it seems that the anomaly is not a duplication of tissue but is in fact a problem which prevents the penile and glanular urethra from meeting.