The association of renal agenesis with ipsilateral blind hemivagina and uterus didelphys is reported as Herlyn-Werner-Wundelich (HWW) syndrome. Presented herein are two cases of HWW syndrome, each with different set of clinical presentations but both with the same arranged diagnostic method and management executed. The first case, 15 year-old nulligravid, manifested severe dysmenorrhea since menarche and is worsening over the past months. On the other hand, the second case, 29 year-old Gravida 1 Para 0 (0010), exhibited cyclic hypogastric pain and gradually enlarging right pelvic mass. Both cases underwent computed tomography scan and ultrasound examination which revealed uterine didelphys, hemivagina obstruction and ipsilateral renal agenesis, yet each has different laterality of mullerian anomaly. Together were managed with full resection of the vaginal septum as well as drainage of the hematometrocolpos, which are, today, the main treatment for patients with HWW syndrome