The present study investigated longitudinal pathways from specific early preschool behavioral problems (ages 2–3 years) to internalizing and externalizing problems in preadolescence (ages 10–11 years), and the role of social problems at school entry (ages 4–5 years) in such pathways. Path analyses were performed using both parent and teacher reports in a sample of 251 to 346 children from the general population, depending on the availability of parent and teacher data at each time of assessment. Structural equation modeling revealed homotypic internalizing and externalizing pathways, predictions from early preschool externalizing problems to later internalizing problems, and negative predictive paths from early internalizing problems to externalizing problems in preadolescence. Cross-informant predictions spanning 8 years were found between parent-reported aggression and overactivity at ages 2–3 years and teacher-reported externalizing problems at ages 10–11 years. Further, results showed that boys' pathways were more complex and showed greater predictive validity than pathways for girls, and that social problems at school entry played a significant role in pathways to internalizing problems, but only for boys. The results are discussed from a developmental psychopathology perspective.