We report on a 80-year-old woman presenting with gross hematuria who was found to have right ureteral transitional cell carcinoma (TCC) and synchronous left renal cell carcinoma (RCC). Laparoscopic left radical nephrectomy with hand assistance and open right partial ureterectomy were performed. Pathology showed right ureteral TCC and left RCC. The simultaneous occurrence of contralateral TCC and RCC is very unusual. However, evaluation of the whole urinary tract is necessary if malignancy is suspected. After the diagnosis is confirmed, an individualized approach must be undertaken for each patient.