ABSTRACT Introduction Laryngotracheal stenosis (LS) is most commonly caused by iatrogenic injury, namely, tracheal intubation. The goal of treatment is the maintenance of a patent airway, which is mostly achieved by surgical intervention. Our objective was to study the effect of perioperative variables on tracheal resection anastomosis (TRA)/cricotracheal resection anastomosis (CTRA) surgical outcomes by identifying statistically significant factors associated with postoperative complications and failure of surgery, i.e., restenosis. Methods Data from the medical records of 33 patients who underwent TRA/CTRA was analyzed by univariate and multivariate logistic regression. The data included perioperative variables such as the etiology of stenosis, comorbidities, and postoperative or long-term complications. Results The study included nine females and 24 males, and most (29, 87.88%) were intubated prior to surgery. Nineteen patients (57.57%) developed one or more postoperative complications, including, but not limited to, surgical site infection and hematoma. Of all patients, six (18.18%) developed long-term restenosis. Multiple factors were significantly associated with the development of postoperative complications. Univariate analysis revealed the following factors as statistically significant: age (p = 0.05), diabetes (p = 0.00001), hypertension (p = 0.00001), and myocardial infarction (p = 0.03). Multivariate analysis showed that age (p = 0.046) and myocardial infarction (p = 0.00001) were independent factors. The study had an overall survival of 97%. Conclusion TRA/CTRA is a complex surgical procedure, and its outcomes can be affected by many factors. More studies with bigger sample sizes are needed to better understand contributing factors and to confirm the already established associations.