Abstract. After sagittal split osteotomy, the mandibular distal and proximal fragments do not always align themselves passively to one another, resulting in bony interferences and subsequent anomalous settlement of the condyles. Predicting these interferences could be an important ancillary procedure for avoiding intra- and postoperative surgical complications, rendering orthognathic surgery more effective and safer. This study evaluated the relevance of virtual surgical planning in assessing the displacement of the proximal segments after virtual distal segment repositioning, for predicting bony interferences between the segments and thus avoiding related intra- and postoperative surgical complications. The presence of interferences between the distal and proximal segments was compared between virtually predicted (computer-assisted simulation surgery, Dolphin software) and real cases in 100 consecutive patients diagnosed with dentofacial deformities who underwent orthognathic surgery with mandibular repositioning (using a short lingual osteotomy (SLO)). The results indicated that clockwise rotation of the mandible was the mandibular movement most prone to segment interference. Furthermore, virtual planning was sensitive (100%) but had low specificity (51.6%) in predicting proximal and distal segment interferences. This low specificity was due to the software-based automated design of the mandibular osteotomy, where the length of the distal segment was longer than the real SLO, and the mandibular ramus sagittal split was located just behind Spix’s spine. Thus, more precise simulated osteotomies are needed to further validate the accuracy of virtual planning for this purpose.