Objective: We discuss the treatment and pathology of simultaneous bilateral metastatic palatine tonsil carcinoma. The current literature of the diagnosis and management of unknown primary oropharyngeal neoplasms is reviewed including the role of positron emission tomography (PET) imaging. Study Design: Squamous cell carcinoma (SCCA) of the palatine tonsil typically presents as a unilateral mass in the oropharynx or as a mass in the ipsilateral neck indicating a lymph node involved with metastasis. The carcinoma rarely presents with involvement of the contralateral lymph nodes, and this situation typically is present only in very advanced local disease. Simultaneous discontiguous disease involving both palatine tonsils is exceedingly rare with less than five cases reported in the medical literature. Methods: Case report and literature review Results: This case report involves a 51 year-old male with bilateral palatine tonsil squamous cell carcinoma and bilateral metastatic neck disease. He presented with a left cystic neck mass diagnosed as squamous cell carcinoma by fine needle aspiration. On exam, the site of the primary tumor was suspected to be ipsilateral tonsil. PET scanning demonstrated asymmetric FDG activity in the contralateral palatine tonsil and neck. The patient underwent bilateral transoral robotic-assisted partial oropharyngectomy demonstrating separate tonsillar carcinomas, both of which were HPV positive. Bilateral neck dissections demonstrated metastatic involvement of one right and two left cervical nodes. Conclusions: We describe an exceedingly rare case of bilateral simultaneous metastatic palatine tonsil SCCA. This finding raises the question regarding the need for bilateral tonsillectomy in the case of the unknown primary or proven tonsil carcinoma with HPV positivity.