Upper urinary tract tumors following an initial diagnosis of bladder cancer are rare. We report a 58-year-old male who presented with gross hematuria and left lumbago for 2 weeks. He had a history of a low-grade, pT1 bladder urothelial carcinoma 24 years previous and had received 5 transurethral resections or biopsies due to suspicion of recurring bladder lesions in the intervening years. A left ureteral tumor was suspected with retrograde pyelography and a computed tomographic scan. Ureteral cancer was confirmed by an endoscopic biopsy. The patient underwent a left nephroureterectomy and bladder cuff excision. The histopathological diagnosis was transitional cell carcinoma. After 20 months of follow-up, the patient was well with no evidence of disease.