We present a rare case of simultaneous occurrence of pleomorphic adenoma of the left parotid gland and squamous cell carcinoma (SCC) of left buccal mucosa in a 59-year-old patient. The synchronous occurrence of these two entities has not been reported in the literature. A PubMed database search did not yield any results for search words involving "Oral Cancer," "Synchronous Oral Cancer and Pleomorphic Adenoma of Parotid gland" and "Oral SCC and Pleomorphic Adenoma of Parotid gland." Furthermore, synchronous development of these two tumors may give rise to diagnostic and ma?nagement conundrums as the parotid growth may be considered to be a nodal metastasis.