Background: The pattern of glenoid bone loss (GBL) in anterior glenohumeral instability is well described. It was recognized recently that posterior GBL after instability has a posteroinferior pattern. Purpose/Hypothesis: The purpose of this study was to compare GBL patterns in a matched cohort of patients with anterior versus posterior glenohumeral instability. The hypothesis was that the GBL pattern in posterior instability would be more inferior than the GBL pattern in anterior instability. Study Design: Cohort study; Level of evidence, 3. Methods: In this multicenter retrospective study, 28 patients with posterior instability were matched with 28 patients with anterior instability by age, sex and number of instability events. GBL location was defined using a clockface model. Obliquity was defined as the angle between the long axis of the glenoid and a line tangent to the GBL. Superior and inferior GBL were measured as areas and defined relative to the equator. The primary outcome was the 2-dimensional characterization of posterior versus anterior GBL. The secondary outcome was a comparison of the posterior GBL patterns in traumatic and atraumatic instability mechanisms in an expanded cohort of 42 patients. Results: The mean age of the matched cohorts (n = 56) was 25.2 ± 9.87 years. The median obliquity of GBL was 27.53° (interquartile range [IQR], 18.83°-47.38°) in the posterior cohort and 9.28° (IQR, 6.68°-15.75°) in the anterior cohort ( P < .001). The mean superior-to-inferior bone loss ratio was 0.48 ± 0.51 in the posterior cohort and 0.80 ± 0.55 ( P = .032) in the anterior cohort. In the expanded posterior instability cohort (n = 42), patients with traumatic injury mechanism (n = 22), had a similar GBL obliquity compared to patients with an atraumatic injury mechanism (n = 20) (mean, 27.73° [95% CI, 20.26°-35.20°] vs 32.20° [95% CI, 21.27°-43.14°], respectively) ( P = .49). Conclusion: Posterior GBL occurred more inferiorly and at an increased obliquity compared with anterior GBL. This pattern is consistent for traumatic and atraumatic posterior GBL. Bone loss along the equator may not be the most reliable predictor of posterior instability, and critical bone loss may be reached more rapidly than a model of loss along the equator may predict.