Despite the fact that the incidence and severity of postoperative complications after oesophagectomy have substantially decreased over the past two decades, anastomotic leakage is still a potentially catastrophic event. In this article, the experience of a single surgical unit is analysed. Over the period from 1992 to 2003, 435 oesophagectomies with oesophagogastroplasty were performed at the Milan University Department of Surgery. The overall mortality rate was 1.6%. The incidence of anastomotic leakage was 8.5% (6.5% for intrathoracic anastomoses and 14% for cervical anastomoses), and the mortality rate due to leakage was 13.5%. The authors discuss the factors associated with anastomotic leakage by comparing their personal experience with data from the international literature.