(1) Background: There is still disagreement over how sleeve gastrectomy (SG) affects gastroesophageal reflux disease (GERD). The debate regarding the best option for patients undergoing bariatric surgery who are also affected by GERD and/or hiatal hernia continues to divide the community of bariatric surgeons. While concomitant hiatal hernia repair (SG + HHR) has been proposed as a means of reducing the risk of GERD following SG with varying degrees of success, the addition of a fundoplication (SG + FP) has been suggested in recent years as a way to improve the lower esophageal sphincter’s competency. The aim of this study is to systematically review and meta-analyze the efficacy of SG + HHR versus SG + FP on GERD remission in patients with obesity. (2) Methods: A systematic review of the literature was conducted, and studies analyzing the effects of SG + HHR versus SG + FP on postoperative GERD were included. The methodological quality of included trials was evaluated. The primary outcome was postoperative GERD rate, erosive esophagitis, and 12-month weight loss. Secondary outcomes included postoperative complications and mortality. The PRISMA guidelines were used to carry out the present systematic review (PROSPERO Registration Number: CRD42023405600). (3) Results: Fifteen articles with a total of 1164 patients were included in the meta-analysis; 554 patients underwent SG + HHR while 610 underwent SG + FP. In the SG + HHR group, 58.5 ± 28.9% of subjects presented clinical GERD symptoms compared to 20.4 ± 17.5% postoperatively (p< 0.001). In the SG + FP group, 64.8 ± 39.4% were affected by GERD preoperatively compared to only 5 ± 8.1% postoperatively (p< 0.001). SG + FP patients had a significantly greater GERD remission compared to SG + HHR (p< 0.001). Weight loss was similar between groups (p= 0.125). The rate of leaks was 0.18% and 0.33% in the SG + HHR and SG + FP, respectively (p= 0.657), while perforations were significantly higher after SG + FP compared to the SG + HHR group (3.1% versus 0%,p= 0.002). The mortality rate was significantly greater in the SG + FP group (0.5% versus 0%,p= 0.002). (4) Conclusions: This study revealed that both SG with concomitant HHR and sleeve–fundoplication are effective in terms of reflux resolution and weight outcomes, with superiority of SG + FP in terms of GERD control, despite a greater overall complication rate. Both strategies can therefore be suggested as a suitable alternative variant to a conventional SG in subjects with obesity and concomitant hiatal hernia and/or GERD. Studies with extended follow-up and direct comparisons of these surgical approaches to conventional SG are warranted.