Risky behaviors represent health risk as well as psychological and social risk for adolescents. Research have shown that personality traits are important predictors of risky and delinquent behavior. The purpose of this study was to examine the relationship between psychopathological personality traits and risky and delinquent behaviors in a sample of secondary school students. The study was conducted on a sample of 449 students (149 male students) from secondary schools in Osijek, Donji Miholjac, Beli Manastir and Đakovo. Participants completed Dimensional Assessment of Personality Traits Questionnaire (DAPTQ) (Krupić and Ručević, 2015), The Personality Inventory for DSM-5 – Brief form (American Psychiatric Association, 2013b) and Youth self-reported delinquency and risk behaviors questionnaire (SRDP; Ručević, Ajduković and Šincek, 2009). It was hypothesized that antagonism, detachment and attention seeking would be correlated with risky and delinquent behaviour. Results of correlation analysis have shown that antagonism is significantly correlated with risky and delinquent behaviours but neither detachment nor attention seeking have shown significant correlations with risky and delinquent behaviours. Results of hierarhical regresion analysis have shown that gender, age, disinhibition, antagonism, compulsivity and grandiosity predicted risky and delinquent behavior.