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Competency-based medical education relies on criterion-referenced assessments to evaluate residents’ progress, yet concerns remain about demographic disparities in Milestone ratings. This retrospective cohort study analyzed data from 4,997 anesthesiology residents across 141 programs, linking Accreditation Council for Graduate Medical Education Milestones with demographic information from the Association of American Medical Colleges. Using three-level mixed-effects models, we examined differences in rating trajectories by gender and race. While baseline ratings showed no consistent disparities, underrepresented in medicine residents exhibited slower growth and significantly lower scores at graduation. Women received lower end-of-training ratings in seven subcompetencies, especially in Patient Care and Medical Knowledge. These findings suggest that modest disparities accumulate over time, underscoring the need for monitoring, faculty training, and equity-focused assessment practices