Background: Determining the amount of glenoid bone loss in patients after anterior glenohumeral instability events is critical to guiding appropriate treatment. One of the challenges in treating the shoulder instability of young athletes is the absence of clear data showing the effect of each event. Purpose: To prospectively determine the amount of bone loss associated with a single instability event in the setting of first-time and recurrent instability. Study Design: Cohort study; Level of evidence, 2. Methods: The authors conducted a prospective cohort study of 714 athletes surveilled for 4 years. Baseline assessment included a subjective history of shoulder instability. Bilateral noncontrast shoulder magnetic resonance imaging (MRI) was obtained for all participants with and without a history of previous shoulder instability. The cohort was prospectively followed during the study period, and those who sustained an anterior glenohumeral instability event were identified. Postinjury MRI with contrast was obtained and compared with the screening MRI. Glenoid width was measured for each patient’s pre- and postinjury MRI. The projected total glenoid bone loss was calculated and compared for patients with a history of shoulder instability. Results: Of the 714 athletes (1428 shoulders) who were prospectively followed during the 4-year period, 22 athletes (23 shoulders) sustained a first-time anterior instability event (5 dislocations, 18 subluxations), and 6 athletes (6 shoulders) with a history of instability sustained a recurrent anterior instability event (1 dislocation, 5 subluxations). On average, there was statistically significant glenoid bone loss (1.84 ± 1.47 mm) after a single instability event (P < .001), equivalent to 6.8% (95% CI, 4.46%-9.04%; range, 0.71%-17.6%) of the glenoid width. After a first-time instability event, 12 shoulders (52%) demonstrated glenoid bone loss ≥5% and 4 shoulders, ≥13.5%; no shoulders had ≥20% glenoid bone loss. Preexisting glenoid bone loss among patients with a history of instability was 10.2% (95% CI, 1.96%-18.35%; range, 0.6%-21.0%). This bone loss increased to 22.8% (95% CI, 20.53%-25.15%; range, 21.2%-26.0%) after additional instability (P = .0117). All 6 shoulders with recurrent instability had ≥20% glenoid bone loss. Conclusion: Glenoid bone loss of 6.8% was observed after a first-time anterior instability event. In the setting of recurrent instability, the total calculated glenoid bone loss was 22.8%, with a high prevalence of bony Bankart lesions (5 of 6). The findings of this study support early stabilization of young active patients after a first-time anterior glenohumeral instability event.