Abstract Background The optimal reconstruction method after radical esophagectomy for esophageal cancer has been under debate. For avoiding an anastomotic stricture, we developed a novel method of circular-stapled esophagogastrostomy by employing the keyhole procedure, which uses a linear stapler (LS) to enlarge the anastomotic opening made with a circular stapler (CS). We report the technique and the clinical outcomes. Methods We retrospectively reviewed 70 patients with esophageal cancer who underwent transthoracic esophagectomy and reconstruction via cervical CS-mediated anastomosis with or without the keyhole procedure between 2018 and 2020. The primary outcome was postoperative anastomotic stricture incidence within 180 days after surgery. Surgical procedures: After a 3.5 cm-wide gastric conduit was created, the blood supply was examined via indocyanine green fluorescence imaging. Usually, anastomosis was made at the site which was dominated by the last branch of the right epiploic artery owing to Kocher’s maneuver. The CS was inserted through the anterior wall of the gastric conduit, and the end-to-side anastomosis was established on the greater curvature side of the gastric conduit. Then, a 45-mm long LS was used to create a keyhole over the circular staples, and the entry hole was closed with a 60-mm long LS. Results Among 70 patients, 22 underwent the keyhole procedure (CS + K group) and the remaining did not (CS group). A smaller CS was used in the CS + K group (p < 0.001). The incidence of anastomotic stricture was significantly different (CS vs. CS + K, 18.8 vs. 0%, p = 0.049), especially when a 21 or 23 mm CS was used (CS vs. CS + K, 50.0 vs. 0%, p = 0.005). The univariate analysis confirmed that CS ≤ 23 without a keyhole was a significant risk factor (p = 0.001). Conclusions The keyhole procedure could be a simple and useful alternative technique that reduces the risk of stricture formation in the cervical esophagogastric anastomosis, especially when using the smaller-sized CS.