The optimal cut-off point of the resection margin was recently debated in oral cancer. To evaluate the current evidence of the dynamic criteria of the resection margin, a review of the available literature was performed. Studies were sourced from PubMed and EMBASE by searching for the keywords "mouth neoplasm", "oral cancer", "oral cavity cancer", "oral squamous cell carcinoma", "tongue cancer", "margins of excision", "surgical margin" and "resection margin". We found approximately 998 articles on PubMed and 2227 articles on EMBASE. A total of 3225 articles was identified, and 2763 of those were left after removing the duplicates. By applying advanced filters about the relevance of the subjects, these were narrowed down to 111 articles. After the final exclusion, 42 full-text articles were reviewed. The universal cut-off criteria of 5 mm used for determining the resection margin status has been debated due to recent studies evaluating the impact of different margin criteria on patient prognosis. Of note, the degree of the microscopic extension from the gross tumor border correlates with tumor dimensions. Therefore, a relatively narrow safety margin can be justified in early-stage oral cancer without the additional risk of recurrence, while a wide safety margin might be required for advanced-stage oral cancer. This review suggests a surgical strategy to adjust the criteria for risk grouping and adjuvant treatments, according to individual tumor dimensions or characteristics. In the future, it might be possible to establish individual tumor-specific surgical margins and risk stratification during or after surgery. However, the results should be interpreted with caution because there is no strong evidence (e.g., prospective randomized controlled studies) yet to support the conclusions. Our study is meaningful in suggesting future research directions and discussions.