How school-associated behavioral problems in childhood and adolescence precede distinctive adult schizotypal symptoms was examined. Gender specific findings were explored. After 11.6 (SD = 3.1) years, 159 patients of the Department of Child and Adolescent Psychiatry of the University Medical Centre Utrecht, the Netherlands were reassessed for adult schizotypal symptoms. Severity of behavioral symptoms in childhood and adolescence using Teacher Report Form (TRF; Verhulst et al. 1997) and adult schizotypal symptoms using Schizotypal Personality Questionnaire-Revised (Raine in Schizophrenia Bulletin 17:555–564, 1991) were examined by Spearman’s bivariate correlations. Multiple regression analyses were performed to determine the combined predictive value of significant TRF subscales for schizotypal symptomatology. Moderation was tested by adding the interactions of gender with TRF subscales to the models. Disregarding gender, correlational analyses revealed that TRF Total problems, in specific thought problems, social problems, and attentional problems were associated with disorganized schizotypal symptoms in adult life. TRF thought problems was also associated with future positive schizotypal symptoms. When gender was taken into account, for boys only thought problems was associated with adult positive schizotypal symptoms, whereas for girls externalizing problems, specifically attentional and aggressive problems, were associated with the higher levels of adult disorganized schizotypal symptoms. Moderated regression analyses provided trend significant evidence confirming that in girls externalizing problems were positively associated with general and disorganized schizotypal symptoms. When using teachers as informants, it was found that juvenile behavioral abnormalities were differentially associated with type of adult schizotypal symptoms, with these associations being further modified by gender.