Renal cell carcinoma uncommonly metastasizes to the ureter, with only rare reports of metastatic lesions developing in the contralateral side. Recently at our institution, two patients presented with contralateral ureteral metastases from a primary renal adenocarcinoma; one was synchronous and the second metachronous. Following extensive metastatic evaluations, both lesions were believed to be solitary metastases. The involved ureters were managed with total ureterectomy and construction of an ileal ureter. We report these two cases and review the literature.