To elucidate the pathophysiology of congenital obstruction of the anterior urethra and to investigate the association between anterior urethral valves and syringocele. Three boys with congenital obstruction of the anterior urethra diagnosed at our department between 1997 and 2004 were analyzed retrospectively. All three boys had congenital obstruction in the bulbar urethra. The presenting symptoms and age of each patient were varied. Whereas continuity between Cowper's duct and the diverticulum was not demonstrated radiographically in all of the boys, it was speculated endoscopically in all. Our series has suggested a possible association between anterior urethral valves (diverticulum) and syringocele. These congenital anomalies of the anterior urethra should be considered in the differential diagnosis of obstructive lesions of the urinary tract.