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Schwannomas are benign tumors composed of neoplastic Schwann cells and rarely occur in the central nervous system. Schwannomas account for approximately 8% of intracranial tumors and most commonly originate from cranial nerve VIII at the cerebellopontine angle in the posterior fossa. Herein, we report two cases of vestibular schwannomas extending in the middle fossa. The first case shows a 51-year-old male who presented with a history of mild headaches for one year associated with acute nausea, vomiting, and word-finding difficulties. Imaging revealed a large multicystic contrast-enhancing lesion in the left middle cranial fossa. The middle fossa lesion was resected with pathology indicating a schwannoma. The second case shows a 63-year-old woman who presented with seizures, right-sided hearing loss, and right-sided facial weakness. On MRI, she is found to have a large right middle fossa lesion originating from the right internal auditory canal and consistent with vestibular schwannoma with a 9 mm leftward midline shift. The histopathologic examination of the excised tumor indicated a schwannoma. Schwannomas most commonly occur in the posterior fossa when they present intracranially. However, in rare occurrences, they may present as middle fossa masses with significant intracranial compression.