Background/Aim: The primary aim was to evaluate the prevalence and localisation of dental injuries caused by osteosynthesis screws during orthognathic surgery, comparing two different CAD/CAM planning/surgical approaches through retrospective evaluation of post-operative computed tomography. Material and Methods: This study considered all patients who underwent orthognathic surgery from 2010–2019. The examination for dental root injuries between conventional osteosynthesis (Maxilla conventional cohort) and osteosynthesis with patient-specific implant (Maxilla PSI cohort) was performed by evaluating the post-operative CT scans. Results: A total of 126 patients were included in the study. Among the 61 patients of the Maxilla conventional cohort, 10 dental root injuries in 8 patients (13.1%) were detected in the post-operative CT scan, representing 1.5% (n= 10/651) of the osteosynthesis screws inserted in proximity of the alveolar crest. No dental injury occurred following osteosynthesis in the 65 patients of the Maxillary PSI cohort (n= 0/773 screws) (p< 0.001). During a mean follow-up period of 13 months after primary surgery, none of the injured teeth showed evidence of periapical alterations and no endodontic treatments were necessary. Conclusions: Maxillary positioning using CAD/CAM-fabricated drill/osteotomy guide and osteosynthesis with PSI can significantly reduce the risk for dental injury compared to the conventional procedure. However, the clinical significance of the detected dental injuries was rather minor.