Objective The aim of this study is to identify clinicopathologic features associated with positive margins after surgical treatment of cutaneous melanoma of the head and neck (CMHN). Study Design Retrospective cohort study. Setting National Cancer Database. Methods A retrospective analysis of the National Cancer Database was performed of patients diagnosed with CMHN between 2004 and 2016. Univariate and multivariate analyses examining the association of clinicopathologic features with positive margins were performed via logistic regression analysis. Results A total of 101,560 patients met inclusion criteria. The incidence of positive margins was 5.0% (5128/101,560). Patients were significantly more likely to have positive margins with the following: increasing age ( P < .001; odds ratio [OR], 1.028; 95% CI, 1.026-1.031), the lip subsite ( P < .001; OR, 1.664; 95% CI, 1.286-2.154), the eyelid subsite ( P < .001; OR, 2.380; 95% CI, 1.996-2.838), the face subsite ( P < .001; OR, 1.215; 95% CI, 1.133-1.302), the lentigo maligna/lentigo maligna melanoma subtype ( P = .019; OR, 1.099; 95% CI, 1.016-1.188), the desmoplastic subtype ( P < .001; OR, 1.455; 95% CI, 1.261-1.680), the spindle cell subtype ( P = .006; OR, 1.276; 95% CI, 1.073-1.516), and advanced pT classification. Patients with male sex ( P < .001; OR, 0.733; 95% CI, 0.687-0.782) and without ulceration ( P < .001; OR, 0.803; 95% CI, 0.736-0.876) were significantly less likely to have positive margins. Conclusion The following have been identified as clinicopathologic features associated with positive margins after surgical treatment of CMHN: increasing age, female sex, the lip subsite, the eyelid subsite, the face subsite, ulceration, the lentigo maligna/lentigo maligna melanoma subtype, the desmoplastic subtype, the spindle cell subtype, and increasing pT classification.