Urothelial carcinoma (UC) or transitional cell carcinoma (TCC) of the bladder has a high likelihood of metastasis, and the more common sites of distant metastasis are bone, liver and lung. Metastasis to the testis is extremely rare. We identified five cases of bladder UC metastasing to the testis in the literature, none of which occurred bilaterally. We present this case of asynchronous UC metastases to both testes as the first report in the literature. Metastatic disease should be considered as a potential differential diagnosis for testicular tumors arising in patients with a history of UC.