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The Accreditation Council for Graduate Medical Education requires biannual evaluation of anesthesiology residents on 25 subcompetency milestones. Some milestone domains are particularly challenging to repeatedly and reliably observe during clinical care. Simulation-Based Milestones Assessment (SBMA) may help overcome these challenges. However, few studies have examined the external validation of simulation assessment scores (ie, the relationships between simulation-based assessment scores and other standard measures of ability) for milestones. This study analyzed whether SBMA scores (1) discriminate by postgraduate year, (2) improve over time, and (3) correlate with traditional measures of performance.This is a retrospective analysis of 55 residents' SBMA data from 30 scenarios for two academic years. Each scenario was evaluated for time-in-training discrimination. Scenarios were then analyzed for SBMA scoring trends over time, and SBMA scores were compared with residents' clinical evaluations.Twenty-four SBMA scenarios discriminated by postgraduate year. Repeated measure analysis of variance showed statistically significant between-session score improvements (F (3, 54) = 17.79, P < 0.001). Pearson correlation coefficients demonstrated moderate to strong correlation between SBMA and clinical evaluations: January 2015 r = 0.67, P < 0.01 (n = 27); May 2015 r = 0.43, P = 0.09 (n = 17); November 2015 r = 0.70, P < 0.01 (n = 24); and April 2016 r = 70, P < 0.01 (n = 27).The associations between SBMA scores and experience level, time-in-training, and clinical performance evaluations provide evidence that SBMA may be used as metrics of residents' Accreditation Council for Graduate Medical Education milestone competencies.