In a quarter of patients with ureterovaginal fistula (UVF), a concurrent associated vesicovaginal fistula (VVF) can also be found. An increased clinical suspicion should be arised in cases of urinary vaginal discharge accompanied with unilateral flank pain following a gynecological procedure. A 43-year-old female patient diagnosed with a complex postoperative UVF and VVF following a total hysterectomy. After an unsuccessful initial conservative approach with the placement of a nephrostomy tube, an ureterocystotomy with antireflux reimplantation of the ureter was decided. The patient experienced an uneventful postoperative period and a year later, the patient remains asymptomatic without any evidence of fistula recurrent. Our case reports the relatively rare presence of a concurrent postoperative complex UVF and VVF formation in order to rise clinical suspicion in clinicians regarding the diagnostic approach and optimal management.