Background: Patients with posterior shoulder instability may have bone and cartilage lesions (BCLs) in addition to capsulolabral injuries, although the risk factors for these intra-articular lesions are unclear. Hypothesis: We hypothesized that patients with posterior instability who had a greater number of instability events would have a higher rate of BCLs compared with patients who had fewer instability episodes. Study Design: Cross-sectional study; Level of evidence, 3. Methods: Data from the Multicenter Orthopaedic Outcomes Network (MOON) Shoulder Group instability patient cohort were analyzed. Patients aged 12 to 99 years undergoing primary surgical treatment for shoulder instability were included. The glenohumeral joint was evaluated by the treating surgeon at the time of surgery, and patients were classified as having a BCL if they had any grade 3 or 4 glenoid or humeral cartilage lesion, reverse Hill-Sachs lesion, bony Bankart lesion, or glenoid bone loss. The effects of the number of instability events on the presence of BCLs was investigated by use of Fisher exact tests. Logistic regression modeling was performed to investigate the independent contributions of demographic variables and injury-specific variables to the likelihood of having a BCL. Significance was defined as P < .05. Results: We identified 271 patients (223 male) for analysis. Bone and cartilage lesions were identified in 54 patients (19.9%) at the time of surgical treatment. A glenoid cartilage injury was most common and was identified in 28 patients (10.3%). A significant difference was noted between the number of instability events and the presence of BCLs (P = .025), with the highest rate observed in patients with 2 to 5 instability events (32.3%). Multivariate logistic regression modeling indicated that increasing age (P = .019) and 2 to 5 reported instability events (P = .001) were significant independent predictors of the presence of BCLs. For bone lesions alone, the number of instability events was the only significant independent predictor; increased risk of bone lesion was present for patients with 1 instability event (OR, 6.1; P = .012), patients with 2 to 5 instability events (OR, 4.2; P = .033), and patients with more than 5 instability events (OR, 6.0; P = .011). Conclusion: Bone and cartilage lesions are seen significantly more frequently with increasing patient age and in patients with 2 to 5 instability events. Early surgical stabilization for posterior instability may be considered to potentially limit the extent of associated intra-articular injury. The group of patients with more than 5 instability events may represent a different pathological condition, as this group showed a decrease in the likelihood of cartilage injury, although not bony injury.