Background: The parapharyngeal space is a complex anatomic area with a wide array of potential pathologies. We present a case report detailing a transoral excision of a parapharyngeal space mass that was found to be a squamous lined cyst and review the anatomic considerations, differential diagnosis, and management of parapharyngeal masses. Case description: A 59-year-old female presented with a sore throat and intermittent left otalgia. Flexible endoscopy was notable for external compression and mass effect of the pharynx and imaging revealed a predominantly cystic mass centered in the left parapharyngeal space displacing the internal carotid artery. Given the appearance and location, the patient underwent transoral excision of a six-centimeter mass that was thought most likely a pleomorphic adenoma or cystic mass. Final pathology revealed a squamous lined cyst with chronic inflammation. Conclusions: The differential for parapharyngeal space masses is extensive and can be roughly grouped into salivary gland, neurogenic, connective tissue, cystic, lymphoid, and metastatic lesions. This broad differential can be narrowed down with radiologic imaging and anatomic understanding. Management is patient-centered and based on tumor size, suspected diagnosis, involved structures, the potential for malignancy, patient comorbidities, and presenting symptoms.