BACKGROUNDMost patients with cutaneous squamous cell carcinoma (cSCC) of the head and neck (HN) are at low‐risk (< 5%) of developing metastatic SCC to regional lymph nodes. However, patients with unfavorable clinicopathologic factors often are under appreciated by clinicians but remain at higher risk for developing metastatic lymph node disease and dying.METHODSPatients were identified who had metastatic cSCC to lymph nodes (parotid and cervical) of the HN and who were treated within the context of a multidisciplinary HN cancer service between 1980 and 2005 at Westmead Hospital (Sydney, Australia). Relevant patient details and data from primary lesions were analyzed and reported.RESULTSIn total, 266 patients were treated with curative intent. The median patient age was 69 years among 219 males and 47 females. The majority of metastatic lymph nodes (162 of 266 lymph nodes; 61%) were located in the parotid with or without cervical lymph node involvement. The median tumor thickness was 6 mm (range, 0.5–28 mm), and the median tumor size was 15 mm (range, 3–70 mm). Most tumors (65%) that measured ≥5 mm in thickness, and 30% of patients had lesions that measured ≥2 cm in greatest dimension. Recurrent cSCC was present in 15% of patients, and most lesions were located within the lymphatic drainage of the parotid on the temple/forehead (28%), on or around the ear (20%), or on the cheek (12%). Forty‐six percent of patients had moderately or poorly differentiated cSCC, and 5% of patients were immunosuppressed. A minority of patients (27%) did not have an identifiable index lesion.CONCLUSIONSData from this large, prospective data base, in concordance with other series, suggested that a patient with thick cSCC (>4–5 mm) located in proximity to the parotid gland can be considered at high‐risk. Increasing lesion size and recurrence contribute to this risk. Cancer 2006. © 2006 American Cancer Society.