Background: Chest drain management has a significant influence on postoperative recovery after robot-assisted minimally invasive esophagectomy (RAMIE). The use of chest drains increases postoperative pain by irritating intercostal nerves and hinders patients from early postoperative mobilization and recovery. To our knowledge, no study has investigated the use of two vs. one intercostal chest drains after RAMIE. Methods: This retrospective cohort study evaluated patients undergoing elective RAMIE with gastric conduit pull-up and intrathoracic anastomosis. Patients were divided into two groups according to placement of one (11/2020–08/2022) or two (08/2018–11/2020) chest drains. Propensity score matching was performed in a 1:1 ratio, and the incidences of overall and pulmonary complications, drainage-associated re-interventions, radiological diagnostics, analgesic use, and length of hospital stay were compared between single drain and double drain groups. Results: During the study period, 194 patients underwent RAMIE. Twenty-two patients were included after propensity score matching in the single and double chest drain group, respectively. Time until removal of the last chest drain [postoperative day (POD) 6.7 ± 4.4 vs. POD 9.4 ± 2.7, p = 0.004] and intensive care unit stay (4.2 ± 5.1 days vs. 5.3 ± 3.5 days, p = 0.01) were significantly shorter in the single drain group. Overall and pulmonary complications, drainage-associated events, re-interventions, number of diagnostic imaging, analgesic use, and length of hospital stay were comparable between both groups. Conclusion: This study is the first to demonstrate the safety of single intercostal chest drain use and, at least, non-inferiority to double chest drains in terms of perioperative complications after RAMIE.