The aim of this study was to explore the relationship between sleep, including both qualitative and quantitative aspects, and delinquent behaviour while controlling for psychopathic features of adolescents and parental supervision at bedtime. We analysed data from a nationally representative sample of 4855 Finnish adolescents (mean age 15.3 years, 51% females). Sleep problems, hours of sleep and delinquency were evaluated via self-report. Psychopathic features were measured with the Antisocial Process Screening Device - Self-Report. In negative binomial regressions, gender and sleep-related variables acted as predictors for both property and violent crime after controlling for psychopathic features and parental supervision at bedtime. The results suggest that both sleep problems (at least three times per week, at least for a year) and an insufficient amount of sleep (less than 7 h) are associated with property crime and violent behaviour, and the relationship is not explained by gender, degree of parental supervision at bedtime or co-occurring psychopathic features. These results suggest that sleep difficulties and insufficient amount of sleep are associated with delinquent behaviour in adolescents. The significance of addressing sleep-related problems, both qualitative and quantitative, among adolescents is thus highlighted. Implications for a prevention technique of delinquent behaviour are discussed.