PURPOSE: The objectives of this study were to retrospectively describe the characteristics and outcomes of patients with oral squamous cell carcinoma (OSCC) with level IV/V metastases, and to evaluate the multivariate relationships among potential risk factors for metastasis and prognosis. MATERIALS AND METHODS: We evaluated 291 patients (178 men and 113 women; mean age, 65.9 ± 13.5 years). Clinicopathological data, time of development of level IV/V metastases, and clinical course were investigated. RESULTS: Twenty-three patients (7.9%) developed level IV/V metastases. The 3-year overall survival rates when level IV/V metastasis first developed were 27.3% upon initial treatment, 57.1% when metachronous neck metastasis developed, and 40.0% when the tumor recurred. Oral tongue tumor subsite, high N staging, neck dissection when metachronous neck metastasis developed, as well as recurrence were independent risk factors for level IV/V metastasis. CONCLUSION: We demonstrate here the multivariate relationships among the risk factors indicated above for level IV/V metastasis and their prognostic significance for patients with OSCC. Oral tongue tumors, high N staging, and neck dissection upon the occurrence of metachronous neck metastasis or recurrence were risk factors for level IV/V metastasis and positive extracapsular spread, presence of multiple lymph metastases, and moderate or poor differentiation were poor prognostic factors.