Synchronous bilateral palatine tonsillar Squamous Cell Carcinoma (SCC) is a rare presentation and less than 10 cases of Human Papillomavirus (HPV) mediated synchronous bilateral palatine tonsillar SCC has been reported. We report case of a patient who presents with a painless left sided neck swelling and was subsequently diagnosed by imaging and histopathology with bilateral Squamous Cell Carcinoma (SCC) of the palatine tonsil and cervical nodal metastasis. Due to its excellent soft tissue/tumor contrast resolution, Magnetic Resonance Imaging (MRI) is the preferred imaging modality for initial staging. Improved sensitivity for the detection of synchronous tumors can be achieved by Positron Emission Tomography (PET)/ Computed Tomography (CT) examination. Due to the rare nature of this pathology, no specific treatment guideline has been provided by National Comprehensive Cancer Network (NCCN). Treatment options available include bilateral Transoral Robotic Surgery (TORS) radical tonsillectomy combined with bilateral neck dissection with adjuvant radiotherapy or chemoradiotherapy and/or upfront concurrent chemoradiotherapy.