There are few options for the treatment of fistulas, leaks, and perforations endoscopically. Here we describe our experience with an endoscopic clipping system. A retrospective review of all cases using the Over-The-Scope-Clip system (Ovesco Endoscopy AG, Tuebingen, Germany) was performed. The system was utilized in ten patients with gastrointestinal surgical complications. Four patients had gastric leaks following sleeve gastrectomy, one had a post-operative colonic leak, two had gastro-gastric fistulas following gastric bypass, and three had esophageal perforations. Two leak patients had complete resolution, one had a contained leak following clip placement that was clinically insignificant, and the fourth patient had a persistent leak despite two clipping procedures. Two patients had gastro-gastric fistulas following roux-en-y gastric bypass surgery and, while they both had initial success, the fistulas recurred. One patient presented with anastomotic leak following colon resection but the system was unable to reach the treatment site. Three patients were successfully treated for esophageal perforation. There were no complications. This over-the-scope endoscopic clip system is simple to use, safe, and successful in approximating tissue to treat traditionally difficult surgical complications. Further experience and longer follow-up are needed to assess its indications as related to defect size and location.