Aim. To analyze long-term outcomes of tracheal transplantation. Material and methods. There were 1128 patients with cicatricial tracheal stenosis who have been operated at the Petrovsky Russian Research Center for Surgery and the Sechenov First Moscow State Medical University for the period 1963—2015. Results. Operations have become safer. Postoperative morbidity and mortality reduced from 41.4% (1963—1980) to 5.6% (2001—2015) and from 21.9% (1963—1980) to 0.5% (2001—2015), respectively. Tracheal transplantation was performed in 2 cases and fundamentally different tracheal structures were applied. Donor thyreotracheal complex with restored blood supply through thyroid vessels was used in the first case (2006). Perennial experimental trials preceded clinical application of this technique. In the second case (2010) we applied scientific results of foreign colleagues (cellular technologies and methods of regenerative medicine to create artificial trachea). Patients are still alive after 12 and 8 years, respectively. Restoration of blood supply of donor trachea is possible through thyroid collaterals. This technique is successful in long-term period. Tissue-engineered trachea cannot be considered true trachea due to no all tracheal components. However, such trachea provides air-conducting, evacuation and protective functions. Tracheomalacia requires further researches as one of the main problems of tracheal transplantation.