Bilateral sagittal split osteotomy (BSSO) is a widely-performed procedure in orthognathic surgery for the correction of dentofacial deformity. Condylar positioning is a critical step during BSSO to maximize functional and morphological results. The unsuitable positioning of condyles represents one of the causative mechanisms that may induce temporomandibular joint noxious effects after BSSO. Repositioning devices can assist surgeons in maintaining the preoperative condylar position; however, empirical repositioning methods based on experience gained are still commonly used. Trainee learning curves are difficult to assess. The aim of this study was to evaluate the relevance of computer-assisted surgery in the acquisition of condylar positioning skills. Forty-eight patients underwent BSSO performed by six maxillofacial trainees (four junior residents and two senior experienced residents). A condyle positioning system (CPS) was used by a senior surgeon to record a condylar position score during the procedure. Firstly, scores were recorded when the trainee manually positioned the condyle without access to the CPS score (phase 1) and then when the trainee positioned the condyle and performed osteosynthesis with visual access to the CPS score (phase 2). Six parameters describing condylar three-dimensional motions were assessed: translational motion from top to bottom (TB), back to front (BF), and left to right (LR), axial rotation (AR), sagittal rotation (SR), frontal rotation (FR), and a total score (TS). There were no significant differences between junior and senior residents in condyle positioning without access to the CPS. Condyles were significantly better positioned during phase 2 with access to the CPS (p<0.001). Over time, use of the CPS (phase 2) produced significantly quicker improvements in scores (p = 0.042). For those teaching surgeries to trainees, computer-assisted devices can potentially result in more rapid learning curves than traditional “observations-imitation” models. Use of a CPS by trainees facilitated condylar repositioning that resulted in an accurate occlusal result and avoidance of adverse effects on the temporomandibular joint.