Dermoid cysts are rare masses of the oral cavity derived from ectodermal elements. These are benign, slow-growing tumors that are typically asymptomatic but cause complications of inflammation or dysphagia, dystonia, and airway encroachment due to mass effects. We report the case of a 17 year old female with a painless mass in the left side of the oral cavity. Ultrasound findings demonstrated non-specific findings of a cystic lesion, and definite diagnosis was made with contrast-enhanced CT and intraoperatively with pathologic confirmation. This retrospective report highlights the challenges in evaluating masses of the oral cavity with imaging and provides a comprehensive discussion on imaging of oral masses on various imaging modalities to guide diagnosis and management.