Tracheostomy and delayed extubation (DE) are two methods for managing patients’ airways postoperatively after oral and maxillofacial free flap transplantation. We aimed to determine the safety of both the tracheostomy and DE by conducting a retrospective study in patients undergoing oral and maxillofacial free-flap transfer from September, 2017 to September, 2022. The primary outcome was incidence of postoperative complication. Secondary outcome was measured as factors leading to perioperative performance of airway management. Ninety-five of 148 patients received delayed extubation perioperatively. In comparison to the tracheostomy group, the DE group had fewer overall postoperative complications (p = 0.028). During the postoperative period, fewer patients from the DE group required a return to the operating room, in comparison to those from the tracheostomy group (p = 0.045). The duration of surgery (p = 0.006), time in ICU (p = 0.015), duration of artificial nutrition (p < 0.001), duration of hospitalization (p < 0.001) in the DE group were all significantly shorter when compared with the tracheostomy group. In conclusion, when used in appropriate cases of oral and maxillofacial free flap transplantation patients, delayed extubation can be a safe and effective alternative to tracheostomy.