Objective: Papillary thyroid carcinoma (PTC) rarely metastasizes to axillary lymph nodes. Although anaplastic transformation (AT) may occur in the cervical lymph node metastasis from PTC, it is rarely observed in the metastatic axillary lymph nodes. Furthermore, cutaneous metastasis from anaplastic thyroid carcinoma (ATC) is extremely rare. Method: A 65-year-old male patient who had operated for multinodular goiter 8 years ago presented with neck swelling on the right side. Residual thyroid tissue was detected and the lesion was removed surgically in combination with a right neck dissection. Histopathologic examination was consistent with PTC and metastatic lymph nodes. The patient received radioactive iodine therapy. Afterwards, the patient presented with a right axillary mass 14 years after the first operation and underwent surgical excision. Results: Histopathologic examination showed PTC with anaplastic transformation. Histopathologically confirmed multiple skin metastases from ATC emerged in thoracic and abdominal regions 3 months after the last operation. Patient died 3 months after the diagnosis of anaplastic carcinoma.