The DSM-oriented approach of the Child Behavior Checklist (CBCL) is a relatively new classification of problem behavior in children and adolescents. Given the clinical and scientific relevance of the CBCL, this study examines similarities and dissimilarities between the empirical and the DSM-oriented approach of the CBCL. We used data from 7,852 children aged 5 and 6 years, whose parents completed the Dutch version of the CBCL/4–18. Spearman rank order correlations, kappas, and logistical regressions were used to examine the similarities and dissimilarities between empirical and DSM-oriented scales of the CBCL. For Total Problems, Internalizing Problems, and Externalizing Problems, we found a substantial agreement between the two approaches of the CBCL. The DSM-oriented syndromes showed a slight overlap with the empirical syndrome scales. With regard to Total Problems, Internalizing Problems, and Externalizing Problems, the same child and family characteristics were associated with elevated scores in both approaches: sex, ethnicity, parental educational level, family composition, and the physician’s identification of the child’s psychosocial problems. Our study shows that both approaches of the CBCL are meaningfully related, but do not identify exactly the same groups of children as deviant. Future studies should explore the differences between the two approaches by examining the correlates and predictive power of both types of scales.