<p>Oral squamous cell carcinoma (OSCC) and basal cell carcinoma (BCC) are epithelial malignancies with distinct etiologies. We report a rare case of synchronous OSCC and BCC in a 62-year-old female with comorbidities. The patient was non-syndromic, obese, and had no history of adverse habits. An initial biopsy of buccal mucosa lesion confirmed moderately differentiated squamous cell carcinoma (grade II). The patient underwent composite resection of the left buccal mucosa lesion along with marginal mandibulectomy and reconstruction. In view of suspicious clinical appearance, excisional biopsy of the adjacent skin lesion was performed. Histopathological examination of the intraoral lesion revealed poorly differentiated squamous cell carcinoma (PDSCC) and extra oral lesion as BCC. The patient was subsequently planned for adjuvant postoperative radiotherapy for buccal mucosal lesion. In conclusion, this case highlights the importance of timely diagnosis and multidisciplinary management for improved outcomes. Clinicians should maintain a high index of suspicion for synchronous malignancies in elderly patients with comorbidities, even in the absence of traditional risk factors.</p>