Background: A multicenter, double-blinded randomized controlled trial comparing isolated Bankart repair (NO REMP) to Bankart repair with remplissage (REMP) reported benefits of remplissage in reducing recurrent instability at 2 years postoperative. The ongoing benefits beyond this time point are yet to be explored. Purpose: To (1) compare medium-term (3 to 9 years) outcomes of these previously randomized patients undergoing isolated Bankart repair (NO REMP) or Bankart repair with remplissage (REMP) to manage recurrent anterior glenohumeral instability; (2) examine the failure rate, overall recurrent instability, and reoperation rate. Study Design: Randomized controlled trial; Level of evidence, 1. Methods: Recruitment and randomization for the original randomized trial occurred between 2011 and 2017. Patients ≥14 years diagnosed with recurrent traumatic anterior shoulder instability with an engaging Hill-Sachs defect of any size were included. Those with a glenoid defect >15% were excluded. In 2020, participants were contacted by telephone and asked standardized questions regarding ensuing instances of subluxation, dislocation, or reoperation on their study shoulder. “Failure” was defined as a redislocation, and “overall recurrent instability” was described as a redislocation or ≥2 subluxations. Descriptive statistics, relative risk, and Kaplan-Meier survival curve analyses were performed. Results: A total of 108 participants were randomized, of whom 50 in the NO REMP group and 52 in the REMP group were included in the analyses in the original study. The mean number of months from surgery to the final follow-up was 49.3 and 53.8 months for the NO REMP and REMP groups, respectively. Failure rates were 22% (11/50) in the NO REMP group versus 8% (4/52) in the REMP group. Rates of overall recurrent instability were 30% (15/50) in the NO REMP group versus 10% (5/52) in the REMP group. Survival curves were significantly different, favoring REMP in both scenarios. Conclusion: For the treatment of traumatic recurrent anterior shoulder instability with a Hill-Sachs lesion and subcritical glenoid bone loss (<15%), a significantly lower rate of overall postoperative recurrent instability was observed with arthroscopic Bankart repair and remplissage than with isolated Bankart repair at a medium-term follow-up (mean of 4 years). Patients who did not receive a remplissage experienced a failure (redislocated) earlier and had a higher rate of revision/reoperation than those who received a concomitant remplissage. Registration: NCT01324531 (ClinicalTrials.gov identifier).