Handwriting is a complex skill to acquire and it requires years of training to be mastered. Children presenting dysgraphia exhibit difficulties automatizing their handwriting. This can bring anxiety and can negatively impact education. 280 children were recruited in schools and specialized clinics to perform the Concise Evaluation Scale for Children’s Handwriting (BHK) on digital tablets. Within this dataset, we identified children with dysgraphia. Twelve digital features describing handwriting through different aspects (static, kinematic, pressure and tilt) were extracted and used to create linear models to investigate handwriting acquisition throughout education. K-means clustering was performed to define a new classification of dysgraphia. Linear models show that three features only (two kinematic and one static) showed a significant association to predict change of handwriting quality in control children. Most kinematic and statics features interacted with age. Results suggest that children with dysgraphia do not simply differ from ones without dysgraphia by quantitative differences on the BHK scale but present a different development in terms of static, kinematic, pressure and tilt features. The K-means clustering yielded 3 clusters (Ci). Children in C1 presented mild dysgraphia usually not detected in schools whereas children in C2 and C3 exhibited severe dysgraphia. Notably, C2 contained individuals displaying abnormalities in term of kinematics and pressure whilst C3 regrouped children showing mainly tilt problems. The current results open new opportunities for automatic detection of children with dysgraphia in classroom. We also believe that the training of pressure and tilt may open new therapeutic opportunities through serious games.