The present study was aimed to investigate the effects of sequencing a two-component surgical procedure for correcting malpositioned jaws (bimaxillary osteotomies); specifically, surgical repositioning of the upper jaw-maxilla, and the lower jaw-mandible. Within a population of 116 patients requiring bimaxillary osteotomies, the investigators analyzed whether there were statistically significant differences in postoperative outcome as measured by concordance with a preoperative digital 3D virtual treatment plan. In one group of subjects (n = 58), the maxillary surgical procedure preceded the mandibular surgery. In the second group (n = 58), the mandibular procedure preceded the maxillary surgical procedure. A semi-automated analysis tool (OrthoGnathicAnalyser) was applied to assess the concordance of the postoperative maxillary and mandibular position with the cone beam CT-based 3D virtual treatment planning in an effort to minimize observer variability. The results demonstrated that in most instances, the maxilla-first surgical approach yielded closer concordance with the 3D virtual treatment plan than a mandibular-first procedure. In selected circumstances, such as a planned counterclockwise rotation of both jaws, the mandible-first sequence resulted in more predictable displacements of the jaws.