Distant metastasis is an uncommon but critical determinant of prognosis in oral squamous cell carcinoma (OSCC). This study aimed to evaluate clinicopathological risk factors associated with distant metastasis and overall survival (OS) in surgically treated patients with OSCC. A retrospective review was conducted on 116 patients who underwent surgery for oral cancer at Samsung Medical Center between 2018 and 2024. Clinicopathological variables—including depth of invasion (DOI), extranodal extension (ENE), lymphovascular invasion (LVI), perineural invasion (PNI), and worst pattern of invasion (WPI)—were analyzed. Kaplan–Meier survival analysis and Cox proportional hazards regression were used to assess prognostic factors. Distant metastasis occurred in 9.1% of patients and was significantly associated with inferior OS (P < 0.0001). In univariate analysis, LVI, ENE, WPI, and multiple metastatic lymph nodes were significantly associated with poor prognosis. Multivariate analysis identified focal LVI as an independent predictor of OS (HR = 14.23, 95% CI: 1.85–109.67, P = 0.011). Subgroup analysis showed a higher frequency of distant metastasis among patients without neck dissection and those with deeper tumor invasion, although statistical significance was not consistently achieved due to limited events. The lung was the most common site of metastasis, and median post-metastatic survival was 5 months. LVI, ENE, WPI, and nodal burden are significant prognostic factors for OSCC. Focal LVI was independently associated with survival. These findings support the integration of high-risk pathological features into postoperative surveillance and treatment planning.