Metastases of head and neck cancers to the axillary lymph nodes are rare. Our review of the literature found only five such reports involving 10 patients. We describe a new case that occurred in a 69-year-old man who presented with a 6-week history of right neck swelling. Positron-emission tomography/computed tomography demonstrated high F18-fluorodeoxyglucose uptake in the neck and also in the right axilla. Fine-needle aspiration cytology revealed squamous cell carcinoma (SCC) at both sites. The patient underwent right-sided radical neck dissection with pectoralis major myocutaneous flap reconstruction and axillary node block dissection. The patient was subsequently treated with chemoradiotherapy, but 6 months later he developed an SCC in the lung. The lung lesion was also treated with chemotherapy, but the patient died 5 months later. Our case is unique among similar cases in that our patient had not undergone any previous treatment of the neck primary. We discuss the mechanism of this unusual presentation.