We report a rare case of transitional cell carcinoma of the urinary bladder metastatic to the orbit, review the histopathology, and highlight characteristics of the few previously reported cases. A 68-year-old man with a remote history of transitional cell carcinoma of the urinary bladder presented with decreased visual acuity, afferent pupillary defect, and limited extraocular motility OS. Computed tomography scan of the orbits showed a diffuse infiltrate surrounding the left globe and optic nerve. Biopsy revealed metastatic transitional cell carcinoma. The patient expired one month later. With only seven cases previously reported, we conclude that transitional cell carcinoma of the urinary bladder rarely metastasizes to the orbit. When present, orbital metastases signify aggressive disease and a poor prognosis. Mean survival following orbital diagnosis is 2.2 months in the cases reported.