Aim: Positive surgical margins are a well-established adverse prognostic factor in oral cavity squamous cell carcinoma (OCSCC); however, the clinical impact and optimal management of positive bony margins remain poorly defined. This study aims to evaluate oncologic outcomes associated with positive bony margins and to propose a practical management algorithm based on institutional experience. Methodology: A retrospective analysis was conducted of patients undergoing surgery for OCSCC between February 2018 and February 2025 at a single tertiary care center. Among 471 operated patients, 123 demonstrated bone invasion, of whom 7 had positive bony margins on histopathology. Data regarding type of resection, timing and site of margin positivity (intraoperative vs postoperative), management strategies, adjuvant treatment, and outcomes were analyzed. All patients had a minimum follow-up of 12 months. Results: Of the 7 patients with positive bony margins, 2 underwent marginal mandibulectomy and 5 segmental mandibulectomy. Re-resection to achieve negative margins was performed in 5 patients, including conversion from marginal to segmental mandibulectomy and additional bone resection. All patients with revised negative bony margins received adjuvant radiotherapy and remained disease-free at follow-up. Two patients with persistent positive bony margins, despite receiving adjuvant concurrent chemoradiotherapy, developed early local recurrence and died. Conclusion: Positive bony margins in OCSCC are associated with poor oncologic outcomes and early local failure. Re-resection to achieve negative margins, when feasible, appears to significantly improve disease control, whereas adjuvant therapy alone may be insufficient in the presence of residual bony disease. A structured management algorithm may aid in clinical decision-making, although larger studies are required to establish standardized guidelines. Conflict of Interest: The authors declare no conflict of interest.