Background: This study aimed to compare clinical outcomes and recurrence of instability after arthroscopic Bankart repair (ABR) in patients with anterior shoulder instability, with and without a GLAD lesion, while distinguishing between primary and recurrent instability. Methods: Consecutive patients who underwent isolated ABR between January 2012 and December 2021 were included. Patients with a concomitant GLAD lesion were matched in with patients without a GLAD lesion according to the following criteria: age, sex, BMI, follow-up time, and primary versus recurrent instability. At minimum two-year follow-up, the clinical outcome (Rowe score, redislocation rate) and the functional outcome, including the American Shoulder and Elbow Surgeons (ASES) score, Western Ontario Shoulder Instability Index (WOSI), Oxford Shoulder Instability Score (OSIS), satisfaction (1–10 scale, 0 = unsatisfied, 10 = very satisfied), and Visual Analogue Scale (VAS), were compared between groups. Results: In total, 28 patients (14 GLAD vs. 14 Bankart; age: 32.5 ± 13.0 years; sex: 92.9% male; BMI: 24.6 ± 2.2) were included 6.9 ± 2.8 (2–11) years after isolated ABR (follow-up rate 63.6%). Clinical and functional outcome did not differ significantly between patients with versus without GLAD lesions (ASES score: 100 [96.5–100] vs. 97.5 [93.3–100], p = 0.27); WOSI (%): 9.0 [3.7–24.5] vs. 3.8 [0.8–8.9], p = 0.22; Rowe score: 90.0 [75.0–100] vs. 95.0 [78.8–100], p = 0.57; OSIS: 46 [44.7–48] vs. 46 [43.0–48], p = 0.54; satisfaction: 8.9 ± 1.4 vs. 8.0 ± 1.4, p = 0.78; VAS 0 [0–1.3] vs. 0 [0–1.0]. In both groups, two patients (14.3%) reported a redislocation during the observation period. Conclusions: At short- to mid-term follow-up, ABR showed favorable outcomes, low dislocation rates, and high patient satisfaction, regardless of the presence of a GLAD lesion or primary versus recurrent instability. However, follow-up time was heterogeneous, and the follow-up rate was marginal.