Transoral robotic surgery (TORS) is performed for both benign as malignant diseases. It has been suggested that patients treated for benign indications may report higher postoperative pain, though supporting evidence is limited. To evaluate which factors are associated with acute postoperative pain severity following TORS. A retrospective observational cohort study was conducted in patients undergoing TORS. Maximum postoperative pain scores (numerical rating scale, NRS 0-10) were recorded for postoperative day (POD) 1,2,3. Clinically well-controlled pain was defined as NRS < 3. Variables including surgical indication (benign or malignant), gender, age, BMI, analgesic use, chronic pain and antidepressant use were analysed. Univariable and multivariable regression analysis were performed for NRS ≥ 3. Of the 119 cases, the mean maximum POD1 pain score was 2.7 (SD 1.89). Univariable analysis showed higher POD1 were associated with benign disease, chronic pain, pain relief, female gender and age. On multivariable regression analysis, only female gender was significantly associated with NRS ≥3. Female gender was found to be the only independent predictor of higher postoperative pain, other factors, including surgical indication were not.