Positive surgical margins in oral cavity squamous cell carcinoma are associated with cost escalation, treatment intensification, and greater risk of recurrence and mortality. The positive margin rate has been decreasing for cT1-T2 oral cavity cancer over the past 2 decades. We aim to evaluate positive margin rates in cT3-T4 oral cavity cancer over time, and determine factors associated with positive margins. Retrospective analysis of a national database. National Cancer Database 2004 to 2018. All adult patients diagnosed between 2004 and 2018 who underwent primary curative intent surgery for previously untreated cT3-T4 oral cavity cancer with known margin status were included. Logistic univariable and multivariable regression analyses were performed to identify factors associated with positive margins. Among 16,326 patients with cT3 or cT4 oral cavity cancer, positive margins were documented in 2932 patients (18.1%). Later year of treatment was not significantly associated with positive margins (odds ratio [OR] 0.98, 95% confidence interval [CI] 0.96-1.00). The proportion of patients treated at academic centers increased over time (OR 1.02, 95% CI 1.01-1.03). On multivariable analysis, positive margins were significantly associated with hard palate primary, cT4 tumors, advancing N stage, lymphovascular invasion, poorly differentiated histology, and treatment at nonacademic or low-volume centers. Despite increased treatment at academic centers for locally advanced oral cavity cancer, there has been no significant decrease in positive margin rates which remains high at 18.1%. Novel techniques for margin planning and assessment may be required to decrease positive margin rates in locally advanced oral cavity cancer.