Oesophagectomy followed by oesophagogastrostomy, in which an anastomosis between the residual oesophagus and the stomach substitute is made, remains the standard surgery for patients with oesophageal cancer. Whichever surgical procedure is chosen, that is, transthoracic oesophagectomy (TTE) with direct visualisation of the thoracic oesophagus or transhiatal oesophagectomy (THE) with avoidance of a thoracic incision, postoperative anastomotic leakage causes considerable morbidity and mortality. Omentoplasty, in which the omentum is used to wrap the anastomosis, has been recommended by some researchers to prevent postoperative anastomotic leakage—one of the most serious complications of oesophagectomy followed by oesophagogastrostomy for patients with oesophageal cancer. This updated systematic review, including 633 participants in three randomised controlled trials, suggests that omentoplasty could reduce the incidence of anastomotic leakage and the duration of hospital stay after operation. Although the difference in anastomotic leakage was significant only among patients undergoing THE, the risk ratios of omentoplasty for THE and TTE were similar. In addition, omentoplasty does not appear to increase or decrease hospital mortality nor the incidence of postoperative complications, such as anastomotic stricture, pulmonary and cardiac complications, infection, vocal cord palsy and perijejunostomy leakage. Additional clinical trials are needed to investigate the influences of omentoplasty on the incidence of anastomotic leakage and anastomotic stricture, long-term survival, duration of hospital stay and quality of life after oesophagectomy and oesophagogastrostomy when different surgical approaches are used.