IMPORTANCE Despite advances in the assessment of technical skills in surgery, a clear understanding of the composites of technical expertise is lacking. Surgical simulation allows for the quantitation of psychomotor skills, generating data sets that can be analyzed using machine learning algorithms. OBJECTIVE To identify surgical and operative factors selected by a machine learning algorithm to accurately classify participants by level of expertise in a virtual reality surgical procedure. DESIGN, SETTING, AND PARTICIPANTS Fifty participants from a single university were recruited between March 1, 2015, and May 31, 2016, to participate in a case series study at McGill University Neurosurgical Simulation and Artificial Intelligence Learning Centre. Data were collected at a single time point and no follow-up data were collected. Individuals were classified a priori as expert (neurosurgery staff), seniors (neurosurgical fellows and senior residents), juniors (neurosurgical junior residents), and medical students, all of whom participated in 250 simulated tumor resections. EXPOSURES All individuals participated in a virtual reality neurosurgical tumor resection scenario. Each scenario was repeated 5 times. MAIN OUTCOMES AND MEASURES Through an iterative process, performance metrics associated with instrument movement and force, resection of tissues, and bleeding generated from the raw simulator data output were selected by K-nearest neighbor, naive Bayes, discriminant analysis, and support vector machine algorithms to most accurately determine group membership. RESULTS A total of 50 individuals (9 women and 41 men; mean [SD] age, 33.6 [9.5] years; 14 neurosurgeons, 4 fellows, 10 senior residents, 10 junior residents, and 12 medical students) participated. Neurosurgeons were in practice between 1 and 25 years, with 9 (64%) involving a predominantly cranial practice. The K-nearest neighbor algorithm had an accuracy of 90% (45 of 50), the naive Bayes algorithm had an accuracy of 84% (42 of 50), the discriminant analysis algorithm had an accuracy of 78% (39 of 50), and the support vector machine algorithm had an accuracy of 76% (38 of 50). The K-nearest neighbor algorithm used 6 performance metrics to classify participants, the naive Bayes algorithm used 9 performance metrics, the discriminant analysis algorithm used 8 performance metrics, and the support vector machine algorithm used 8 performance metrics. Two neurosurgeons, 1 fellow or senior resident, 1 junior resident, and 1 medical student were misclassified. CONCLUSIONS AND RELEVANCE In a virtual reality neurosurgical tumor resection study, a machine learning algorithm successfully classified participants into 4 levels of expertise with 90% accuracy.