A 24-year-old woman presented with right face pain and blurry vision. Examination revealed right pupil-sparing third nerve palsy and decreased sensation in the second and third divisions of the right trigeminal nerve. MRI demonstrated right cavernous sinus enhancement. Infectious, rheumatologic, and neoplastic evaluation was negative, and the patient was diagnosed with Tolosa-Hunt syndrome. Corticosteroid therapy resulted in resolution of all symptoms. Ten months later, the patient developed left face pain and double vision with a left third nerve palsy on examination. MRI revealed an enhancing left cavernous sinus. High-dose corticosteroid therapy again led to resolution of symptoms. This case demonstrates that Tolosa-Hunt syndrome can rarely recur on the contralateral side. MRI of this presentation has not been previously reported in the literature.