Surgical resection of head and neck (H&N) neoplasms requiring osseous reconstruction have underdefined complication profiles. This study aimed to characterize postoperative outcomes of patients with H&N neoplasia undergoing osteocutaneous flap (OCF) or bare bone flap (BBF) reconstructions. Retrospective analysis of the National Surgical Quality Improvement Program (NSQIP) 2005-2017 databases. Queried for diagnosis and procedural codes extracted patients with H&N neoplasms undergoing BBF or OCF reconstruction. Postoperative complications were evaluated. Multivariable regression generated adjusted odds ratios. A cohort of 746 patients were identified. Of reconstructions, 24.9% (n = 186/746) were BBFs while 75.1% (n = 560/746) were OCFs. 58.1% of the BBF cohort and 59.9% of the OCF cohort experienced an all-cause complication (p = .654). Sub-stratified, 24.2% of BBF and 17.5% of OCF patients experienced a wound complication (p = .045). Regression analysis demonstrated no difference in risk for medical complications between cohorts. However, patients receiving OCFs had a decreased likelihood of developing a wound complication (OR 0.652; 95%CI 0.430-0.989; p = .044) compared to patients receiving BBFs. The incidence of complications following osseous reconstruction of the H&N is considerable. Although several complication outcomes do not seem to differ between BBF or OCF reconstructions, OCFs is associated with a decreased likelihood of wound complications.