Tolosa-Hunt syndrome is an idiopathic, inflammatory condition involving the cavernous sinus and is characterized by unilateral, painful ophthalmoparesis. The condition often begins with retro-orbital pain followed by select cranial nerve involvement. We report the case of a 17-year-old female whose presentation with progressive left-sided headache and ophthalmoparesis culminated in the diagnosis of Tolosa-Hunt syndrome. While many of her signs and symptoms have been previously reported in the rare pediatric cases of Tolosa-Hunt syndrome described in the literature, this case illustrates a unique presentation involving cranial nerves V and VII in addition to the more commonly reported cranial nerve III, IV, and VI palsies.