ABSTRACT Background: Contralateral nodal recurrence (CNR) in well-lateralised oral cavity squamous cell carcinoma (OCSCC) is uncommon but clinically significant, often associated with poor survival outcomes. The benefit of elective contralateral neck treatment remains uncertain, and established prognostic indicators for CNR are limited. Objective: To identify clinicopathological and radiological predictors of CNR and evaluate their impact on contralateral nodal recurrence-free survival (CNRFS) in patients with well-lateralised OCSCC. Methods: A mixed retrospective and prospective cohort study was conducted at a tertiary cancer centre in India between January 2020 and December 2024. Patients with well-lateralised OCSCC undergoing surgery with or without adjuvant therapy were included. Clinical, imaging, and pathological variables were assessed using univariate and multivariate Cox regression analyses. CRNRFS and overall survival (OS) were estimated using the Kaplan-Meier method. Results: Among 498 patients, 49 (9.8%) developed CNR. Multivariate analysis identified several independent predictors: advanced pathological nodal stage, multiple positive lymph nodes (HR 3.25, p=0.0006), and advanced T stage (T3–T4, HR 2.48, p=0.0012). Clinical and pathological extranodal extension (ENE) and lymphovascular invasion (LVI) were significant on univariate analysis but not independent predictors. Median time to CNR was 17 months. Patients with pathological extranodal extension had the lowest contralateral nodal recurrence-free survival (10%). Conclusion: Contralateral nodal recurrence occurred in approximately 10% of patients with well-lateralised oral cavity squamous cell carcinoma. Key predictors were nodal burden, tumour stage, and radiological findings. These findings support a risk-adapted approach, reserving elective contralateral neck treatment for patients with high-risk disease features.