Background: Maxillomandibular advancement (MMA) has been shown to be the most effective surgical therapy for obstructive sleep apnea (OSA). Despite high success rates, there are patients who are considered as non-responders to MMA. In order to triage and inform these patients on their expected prognosis of MMA before the surgery, this study aimed to develop, internally validate, and calibrate a prediction model for the presence of surgical success for MMA in patients with OSA. Methods: A retrospective cohort study was conducted that included patients that had undergone MMA for moderate to severe OSA. Baseline clinical, polysomnographic, cephalometric, and drug-induced sleep endoscopy findings were recorded as potential predictors. Presence or absence of surgical success was recorded as outcome. Binary logistic regression analyses were conducted to develop the model. Performance and clinical values of the model were analyzed. Results: One hundred patients were included, of which sixty-seven (67%) patients reached surgical success. Anterior lower face height (ALFH) (OR: 0.93 [0.87–1.00], p = 0.05), superior posterior airway space (SPAS) (OR: 0.76 [0.62–0.92], p < 0.05), age (OR: 0.96 [0.91–1.01], p = 0.13), and a central apnea index (CAI) <5 events/hour sleep (OR: 0.16 [0.03–0.91], p < 0.05) were significant independent predictors in the model (significance level set at p = 0.20). The model showed acceptable discrimination with a shrunken area under the curve of 0.74, and acceptable calibration. The added predictive values for ruling in and out of surgical success were 0.21 and 0.32, respectively. Conclusions: Lower age at surgery, CAI < 5 events/hour, lower ALFH, and smaller SPAS were significant predictors for the surgical success of MMA. The discrimination, calibration, and clinical added values of the model were acceptable.