Objective: To examine the extent to which preschool emotional and behavioral regulatory difficulties were associated with an increased risk of later mental health and educational problems. Of particular interest was whether early regulatory abilities contributed to later risk once baseline child behavioral adjustment and cognitive function were taken into account. Method: Data were drawn from a prospective longitudinal study of 223 children born very preterm (VPT; <32 weeks gestation, n = 110) and full term (37-40 weeks gestation). At corrected ages 2 and 4 years, children's regulatory abilities were assessed using (1) direct observation of child behavior, (2) a modified version of the Emotion Regulation Checklist, and (3) tester ratings of child behavior during neuropsychological testing. At age 9 years, mental health and educational achievement were assessed using the Development and Well-being Assessment interview and the Woodcock Johnson-III Tests of Achievement. Results: VPT-born children had poorer emotional and behavioral regulation across all measures and time points. They also had higher rates of DSM-IV mental health disorder and educational delay at age 9. Across both study groups, poorer self regulation was associated with an increased risk of ADHD, conduct disorder, anxiety disorders and any disorder net of preschool child behavior problems and social risk. In contrast, only associations between early regulation and later language and any educational delay remained significant after adjustment for preschool cognitive functioning and family social risk. Conclusion: Early assessment of regulation in addition to behavioral screening may improve the early identification of preschool children at mental health risk.