The primary aim of this study was to assess the association between clinical efficacy outcomes (i.e., polysomnography (PSG) results) of maxillomandibular advancement (MMA) and surgeons’ experience. The second aim was to assess the association between the occurrence of postoperative complications of MMA and surgeons’ experiences. Patients treated with MMA for moderate to severe obstructive sleep apnea (OSA) were enrolled in this retrospective study. The patient population was divided into two groups based on two different surgeons performing MMA. The associations between surgeons’ experience on the one hand and PSG results and postoperative complications on the other hand were investigated. A total of 75 patients were included. There was no significant difference in baseline characteristics between the two groups. The reductions in apnea-hypopnea index and oxygen desaturation index were both significantly greater in group-B than group-A (p= 0.015 and 0.002, respectively). The overall success rate after MMA was 64.0%. There was a negative correlation between surgeon experience and surgical success (odds ratio: 0.963 [0.93, 1.00],p= 0.031). No significant association was found between surgeon experience and surgical cure. Additionally, there was no significant association between surgeon experience and the occurrence of postoperative complications. Within the limitations of this study, it is concluded that surgeon experience may have little to no influence on the clinical efficacy and safety of MMA surgery in OSA patients.