This retrospective cohort study compares the virtual planned and postoperative jaw positions in patients undergoing orthognathic surgery. Surgery was virtually planned with the Digital Münster Model Surgery system (DMMS). Primary outcome: Spatial difference in the maxillo-mandibulo relation between virtual planning and postoperative result. Secondary outcome: Possible relationship between the measured differences and surgical movements as well as the postoperative stability according to Proffit. Ninety female and sixty-one male patients were included in the study. The average translation errors were 0.54 ± 0.50 mm (anteroposterior), 0.37 ± 0.33 mm (mediolateral), and 0.33 ± 0.28 mm (superoinferior). Orientation errors were 0.86 ± 0.79 degrees (yaw), 0.54 ± 0.48 degrees (roll), and 0.90 ± 0.72 degrees (pitch). The surgical procedures do not differ with respect to their error sizes. Maxilla forward and class II maxilla up with mandible forward are the most precise procedures. Most significant differences were found in the anteroposterior direction, whereby the extent of the surgical movement has no effect on the magnitude of the error. The process of planning with the DMMS followed by surgery is highly accurate and shows error values well below the clinically accepted limit of two millimeters in translation and four degrees in rotation.