There are very few case reports of the diagnosis and management of concurrent oral cavity and parapharyngeal space tumors. We present a case involving a 49-year-old female who presented with oral cavity squamous cell carcinoma confirmed by biopsy. Initial diagnostic workup revealed a concurrent parapharyngeal mass. Diagnostic studies and surgical therapy were tailored to account for both pathological entities. The patient was treated with a combination of surgery and adjuvant therapy. The surgical strategy was designed to address both lesions simultaneously. One year post-surgery, the patient had good response to therapy with no evidence of persistent or recurrent disease. This report discusses the outcome and treatment of a rare case of concurrent squamous cell carcinoma with a complicating parapharyngeal space tumor. It explores the diagnostic process, comprehensive workup, and the surgical management.