A man in his 80s presented with severe dysphagia. He had undergone pharyngectomy and reconstruction using pectoral major musculo-cutaneous flap for hypopharyngeal cancer. Postoperatively, appearing stenosis of the pharyngeal flap anastomosis. At our hospital, a small-caliber endoscope was inserted through a gastrostomy and advanced retrogradely to obstruction site. Under rendezvous guidance, the stenosis was incised orally using a high-frequency knife. Although luminal patency was temporally restored, repeated restenosis occurred, and a covered esophageal stent was placed. Then, he was admitted to our hospital with restenosis at the anastomotic site. Using an oral endoscope, the stent was removed and reinserted. We report a case of esophageal stent placement using a rendezvous technique involving both oral and gastrostomy approaches.