Introduction: A synchronous second primary malignancy as squamous cell carcinoma of external acoustic meatus following basal cell carcinoma of cheek is reported with their management and review of literature. Case Report: Pigmented basal cell carcinoma of cheek was managed successfully by wide local excision followed by flap reconstruction and subsequently diagnosed squamous cell carcinoma of external acoustic meatus by concurrent chemoradiation after initial surgical debridement. Conclusion: Second primary malignancy as squamous cell carcinoma of external ear canal is rare after basal cell carcinoma of cheek though there is anatomical vicinity. Surgery in case of basal cell carcinoma and concurrent chemoradiotherapy in case of external ear canal squamous cell carcinoma is the mainstay of treatment.