Background: The present study aims to compare the accuracy of jaw repositioning in bimaxillary orthognathic surgery using digital surgical planning in cleft lip and palate patients and in non-syndromic skeletal class III patients in order to investigate if orthognathic surgery achieves different results in the first group of patients. Method: This study included 32 class III adult patients divided into 2 groups: cleft lip and palate (A, n = 16) and non-cleft (B, n = 16). For each patient, a 2D pre-surgical visual treatment objective was performed by the surgeon to predict hard tissue changes, and the surgical outcome was compared with that planned by using cephalometric measurement (ANB, SNA, SNB, Ar-Go-Me, S-Ar-Go). The statistical analysis showed equivalence between obtained and planned results for each measurement both in group A and in group B, but the difference between the planned and the obtained result was smaller in group B regarding ANB angle. Conclusions: Digital surgical planning ensures better predictability of the surgical results and higher accuracy of surgery in complex patients, such as those with cleft lip and palate.