Premature infants have significant risk for later behavior problems. This study examined growth trajectories of three problem behaviors across five developmental age points from preschool to early adulthood in a well-characterized sample of premature infants. The effects of neonatal risk, gender, and socioeconomic context were modeled on these trajectories. The longitudinal sample was comprised of preterm infants (N = 160) with full variation of neonatal morbidity and birth weight (640-1,950 g). Trajectories of externalizing, internalizing and attention problem behaviors from 4 to 23 years, measured by the Child Behavior Checklist, were tested using latent growth curve modeling. The results indicate individual variation in the number of externalizing and internalizing problems over time. Externalizing problems were not significantly different for males and females, but male scores were consistently higher. Neonatal risk was significantly associated with higher internalizing problems at age 4, but was not predictive at school age and beyond. Attention-problem scores increased from early preschool through adolescence for males, but females had little change over the same ages. SES was not predictive of any problem behavior trajectories and no significant two-way interactions were found. The results advance understanding of stability and change of three important problem behaviors through preschool, childhood, and adolescence to young adulthood in prematurely born infants in order to inform clinicians about timely assessment and the refinement of effective interventions.