The aim of this study was to analyze a novel digital technique to quantify the distal tooth displacement and derotation angle produced by the Carriere Motion Appliance (CMA). Twenty-one patients with a class II molar and canine relationship underwent orthodontic treatment with CMA. All patients were exposed before (STL1) and after the CMA placement (STL2), submitted to a digital impression, and afterwards, data were uploaded to specific cephalometric software to allow automatic mesh network alignment of the STL digital files. Subsequently, the distal tooth displacement of the upper canines and first upper molars, as well as the derotation angle of the first upper molars were analyzed using the Pearson correlation coefficient (ρ). Repeatability and reproducibility were analyzed using Gage R&R statistical analysis. An increase in canine displacement was correlated with an increase in contralateral canine displacement (ρ = 0.759;p< 0.000). An increase in canine displacement was correlated with an increase in molar displacement (ρ = 0.715;p< 0.001). An increase in upper first molar displacement was correlated with an increase in the contralateral upper first molar displacement (ρ = 0.609;p< 0.003) and the canine displacement (ρ = 0.728;p< 0.001). The distal tooth displacement showed a repeatability of 0.62% and reproducibility of 7.49%, and the derotation angle showed a repeatability of 0.30% and reproducibility of 0.12%. The novel digital measurement technique is a reproducible, repeatable, and accurate method for quantifying the distal tooth displacement of the upper canine and first upper molar, as well as the derotation angle of the first upper molars after using CMA.