Handwriting problems impact school achievement. The purpose of this pilot study was to evaluate the agreement between teachers’ opinions and the German Systematische Erfassung motorischer Schreibstörungen’s (SEMS) handwriting test and to estimate the prevalence of handwriting problems. This was a prospective, correlational study. Teachers’ ratings of handwriting from German children (Grades 2 and 4) were compared to SEMS scores. The agreement was calculated with Gwet’s AC2; preliminary cutoffs and prevalence were assessed with receiver–operating characteristic curves. SEMS accurately identified Grade 2 children with handwriting problems (specificity = 98.21%, sensitivity = 100%) but fewer Grade 4 children with handwriting difficulties than did teachers (specificity 97.67%, sensitivity 28.57%). Grade 4 item agreement supports the SEMS’ ability to assess underlying handwriting dimensions as perceived by teachers. Teachers identified 12.70% of Grade 2 children versus SEMS 11.11% and 14% of Grade 4 children versus SEMS 6%. The SEMS supports clinical observations and provides information about underlying handwriting dimensions. Because handwriting is used primarily at school, the opinions of teachers are also critical.