To listen to the podcast associated with this article, please select one of the following: iTunes, Google Play, or direct download. OBJECTIVE. The purpose of this study is to determine the most accurate imaging techniques to measure glenoid bone loss in anterior glenohumeral instability through a systematic review of existing literature. MATERIALS AND METHODS. We performed a comprehensive literature search of five databases for original research measuring glenoid bone loss at radiography, CT, or MRI, using prospective or retrospective cohort, case-control, or cadaveric study designs up to January 2018. The Quality Assessment of Diagnostic Accuracy Studies-2 tool aided qualitative assessment of the methods. Data extraction included results, index test interobserver agreement, and accuracy analysis. RESULTS. Twenty-seven studies (evaluating 1425 shoulders) met inclusion criteria after full-text review by two independent readers. Glenoid bone loss was assessed, comparing several index tests to nonimaging (n = 18 studies) and imaging (n = 11) reference standards. Compared with arthroscopic or cadaveric measurements, 2D CT was accurate in six of seven studies (86%), 3D CT was accurate in eight of 10 studies (80%), 2D MRI was accurate in five of seven studies (71%), 3D MRI was accurate in four of four studies (100%), and radiographs were accurate in zero of four studies (0%). Best-fit circle methods (glenoid width or Pico surface area) were the most common and both were accurate (86-90% and 75-100%, respectively) using CT and MRI. Studies had good external validity (78%). Most risk for bias arose from patient selection and reference standards. Only two studies reported sensitivity and specificity, both comparing CT to arthroscopy using different bone loss thresholds (20% and 25%). CONCLUSION. CT and MRI (2D or 3D) accurately measure glenoid bone loss in anterior shoulder instability, but radiographs do not. Best-fit circle measurement techniques are reliable and accurate. Current literature about glenoid bone loss is heterogeneous, and future studies should focus on diagnosis of clinically relevant glenoid bone loss.