Transitional cell carcinoma (TCC) has been well described for its propensity to metastasize to distant sites. Metastases to the soft tissues of the oral cavity from a bladder cancer are extremely rare. We present the case of a 65-year-old man who presented with history of hematuria for 1 month and was found to have high-grade TCC of the bladder. He developed a cheek lesion after 3 weeks, which was diagnosed as metastatic nodule along with pulmonary metastases from high-grade bladder TCC. The patient received chemotherapy followed by the radiotherapy of the cheek lesion, but he succumbed after 3 months due widespread metastatic disease. We also presented a review of the literature regarding this rare presentation.