A 37-year-old woman presented with diplopia caused by a metastatic mandibular ameloblastoma to the cavernous sinus and subsequent spread to the orbit. Initial treatment consisted of local curretage and two local recurrences occurred prior to the cavernous sinus metastasis nine years after presentation. Although considered a benign tumor, ameloblastoma may metastasize despite a benign histologic appearance, Since metastases most often occur after multiple local recurrences, initial radical surgery should be performed.