The purpose of this study was to develop a complete digital workflow for planning, simulation, and evaluation for orthognathic surgery based on 3D digital natural head position reproduction, a cloud-based collaboration platform, and 3D landmark-based evaluation. We included 24 patients who underwent bimaxillary orthognathic surgery. Surgeons and engineers could share the massive image data immediately and conveniently and collaborate closely in surgical planning and simulation using a cloud-based platform. The digital surgical splint could be optimized for a specific patient before or after the physical fabrication of 3D printing splints through close collaboration. The surgical accuracy was evaluated comprehensively via the translational (linear) and rotational (angular) discrepancies between identical 3D landmarks on the simulation and postoperative computed tomography (CT) models. The means of the absolute linear discrepancy at eight tooth landmarks were 0.61 ± 0.55, 0.86 ± 0.68, and 1.00 ± 0.79 mm in left–right, advance–setback, and impaction–elongation directions, respectively, and 1.67 mm in the root mean square direction. The linear discrepancy in the left–right direction was significantly different from the other two directions as shown by analysis of variance (ANOVA, p < 0.05). The means of the absolute angular discrepancies were 1.43 ± 1.06°, 0.50 ± 0.31°, and 0.58 ± 0.41° in the pitch, roll, and yaw orientations, respectively. The angular discrepancy in the pitch orientation was significantly different from the other two orientations (ANOVA, p < 0.05). The complete digital workflow that we developed for orthognathic patients provides efficient and streamlined procedures for orthognathic surgery and shows high surgical accuracy with efficient image data sharing and close collaboration.