Conclusion: Preoperative chemoradiotherapy (CRT) was associated with a significantly higher rate of pharyngocutaneous fistula (PCF). Objective: PCF is the most frequent complication following total laryngectomy. Although organ-preserving radiotherapy (RT) or CRT offer good locoregional control, many patients still require salvage laryngectomy. The aim of this study was to evaluate the factors that predispose patients to PCF, with a focus on preoperative RT, induction chemotherapy (ICT), and CRT. Methods: This was a retrospective case series; 151 patients who underwent TL were reviewed. Preoperative RT, ICT, CRT, and some surgical parameters were analyzed as potential risk factors. Results: The overall PCF rate was 13%. CRT was the only preoperative treatment that had a significant effect on PCF (35.3%, p = 0.004, odds ratio (OR) = 10.75). Surgery extended to the pharynx (p = 0.005, OR = 8.34) and vacuum drain duration (p = 0.012, OR = 5.16) were observed to be associated with PCF.