Objectives: This prospective observational study aimed to assess the clinical outcomes of perioperative airway and ventilatory management in patients undergoing surgery for oral cavity cancer. The study described the frequencies and types of procedures for securing the airway and the duration and types of postoperative ventilatory support. We compared the findings with those of the TRACHY study. Patients and Methods: One hundred patients undergoing oral cavity oncological surgeries were included. Airway assessment included inter-incisor gap, Mallampati class, neck movements, and radiological features. Surgical parameters, postoperative ventilatory support, and complications were documented. Results: The buccal mucosa was the most common cancer site (48.0%), and direct laryngoscopy was deemed difficult in 58.0% of patients. Awake fibreoptic intubation or elective tracheostomy was required in 43.0% of cases. Thirty-three patients were extubated on the table, and 34 patients were successfully managed with a delayed extubation strategy. In comparison with the TRACHY study, variations were observed in demographic parameters, tumour characteristics, and surgical interventions. Our mean TRACHY score was 1.38, and only five patients had a score ≥4. Prophylactic tra-cheostomy was performed in 2.0% of cases, in contrast to the TRACHY study in which 42.0% of patients underwent the procedure. Conclusion The study emphasizes the challenges in airway management for oral cavity cancer surgery. While prophylactic tracheostomy may be necessary in specific cases, individualized approaches, including delayed extubation, are preferrable to maximize safety. Our findings contribute to better understanding and managing perioperative challenges in oral cancer patients and highlight the need for personalized strategies. Scoring systems like TRACHY should not be accepted as universally applicable.