OBJECTIVE: The aim of this study was to evaluate the complication rates for third molar extractions, based on resident level within an oral and maxillofacial surgery program, and to identify the risk factors associated with postoperative complications following third molar extractions. STUDY DESIGN: Records of 1992 patients (5466 third molar extractions) over a 5-year period were reviewed. Data were collected by using appropriate Current Dental Terminology codes from July 1, 2011, to June 30, 2016. The cases were analyzed by using demographic statistics, Pearson chi(2) test, and regression analysis. RESULTS: Of the total number of patients, 1855 had sufficient data available for analysis and inclusion in the study. There were 146 adverse outcomes. The common complication was alveolar osteitis. Nerve injuries and retained root tips were encountered less frequently. There was a significant association between the depth of impaction and developing a postoperative complication. There was a direct correlation between the level of resident training and the likelihood of an adverse outcome. CONCLUSIONS: The study indicates that there are identifiable risk factors associated with postoperative complications following third molar extraction in an oral and maxillofacial surgery residency program. These factors include location, depth of impaction, use of a surgical drill, and level of resident training, which are correlated directly with the development of negative outcomes following third molar extractions.