Ovarian metastases from a primary urinary tract carcinoma are extremely rare. This can be difficult to distinguish from transitional cell carcinomas (TCC) of ovarian origin because of histologic similarity. A 65-year-old woman who was diagnosed with renal pelvis TCC 4 months prior was referred for evaluation of a left ovarian mass. A 47-year-old woman who underwent radical cystectomy due to bladder TCC 1 year ago was referred because of a right ovarian mass. Both patients underwent a bilateral salpingo-oophorectomy. The tumor cells had morphology identical to those of the primary urinary tract tumors. Gynecologic oncologists should consider metastatic TCC of the ovary from urinary tract origin, as well as breast, and gastrointestinal tract origins.