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To study perinatal risk factors for psychiatric symptoms in adolescents born preterm with very low birth weight or at term, but small for gestational age (GA).Mental health was assessed in 65 adolescents born with very low birth weight (VLBW) (birth weight ≤1500 g), 59 born term small for GA (birth weight <10th centile) and 81 control adolescents using Schedule for Affective Disorders and Schizophrenia for School-Age Children, Children's Global Assessment Scale, Autism Spectrum Screening Questionnaire, Attention-Deficit Hyperactivity Disorder-Rating Scale IV and Achenbach System of Empirically Based Assessment. Perinatal data included birth weight, GA, head circumference, Apgar scores, intraventricular hemorrhage, days in neonatal intensive care unit, and days on mechanical ventilation.In the very low birth weight group, lower birth weight was associated with inattention (p < .01), psychiatric diagnoses, and reduced psychosocial function (p ≤ .05). Intraventricular hemorrhage increased the risk for a high inattention score (odds ratio = 7.5; 95% confidence intervals: 1.2–46.8). Lower Apgar score at 1 min was associated with a high Autism Spectrum Screening Questionnaire score and lower Apgar score at 5 min with a high internalizing score (p ≤ .05). In the subgroup born appropriate for GA, internalizing symptoms were also associated with lower GA. In the term small for GA group, perinatal events were not associated with psychiatric problems. In contrast, low socioeconomic status was associated with externalizing symptoms.Lower birth weight, shorter gestation, and intraventricular hemorrhage were risk factors for psychiatric problems in the very low birth weight group. Lower Apgar score increased the risk for autism spectrum symptoms and internalizing symptoms. Among adolescents born term small for GA, the main risk factor for psychiatric symptoms was low socioeconomic status.