OBJECTIVE: The Accreditation Council for Graduate Medical Education requires accredited general surgery residencies to implement competency-based developmental outcomes in resident evaluations. Overall, 16 milestones are evaluated by a clinical competency committee (CCC). The milestones span 8 domains of surgical practice and 6 Accreditation Council for Graduate Medical Education clinical competencies. The highest level suggests preparedness for independent practice. Our objective was to compare self-assessments and committee evaluations within the milestone framework. STUDY DESIGN: All residents underwent semiannual evaluations from 2013 to 2015. Residents independently completed a self-assessment using the milestones. The CCC completed the milestones document using resident evaluations and consensus opinion of committee members. Assessment differences were calculated for each evaluation. A negative value indicated that the residents evaluated themselves at a lower level than the committee. Major assessment disparities were defined as >0.5 on a 4-point scale. SETTING: An independent academic medical center. PARTICIPANTS: General surgery residents. RESULTS: Overall, 20 residents participated; 7 were female. In total, 5 (7%) evaluations had a mean overall assessment difference >0.5, whereas 6 (8%) had a difference <-0.5. Residents evaluated themselves lower than the committee with a median assessment difference of -0.06 [-0.25 to 0.16] (p = 0.041). Evaluations were similar across surgical domains. Negative self-evaluations were more common for medical knowledge (-0.25 [-0.25 to 0.25], p = 0.025). Female residents had 2% positive and 13% negative major assessment disparity rates versus 10% positive and 9% negative rates among male residents. Postgraduate year III residents had 12% positive and 4% negative major disparity rates; all other years had higher negative than positive rates. CONCLUSIONS: Surgery residents within our program demonstrated adequate self-awareness, with most self-evaluations falling within a half level of the CCC report. This self-awareness was consistent across surgical domains and most clinical competencies. Residents perceived a lower level of medical knowledge than the CCC. Subgroup analysis revealed interesting trends in the effects of sex, postgraduate year level, and academic year timing, which will take additional study to fully delineate.