Testosterone (T) has been found to have a stimulating effect on aggressive behavior in a wide range of vertebrate species. There is also some evidence of a positive relationship in humans, albeit less consistently. In the present study we investigated the relationship between T and aggression, dominance and delinquency over time, covering a period from early adolescence to adulthood. From a large population-based sample (n = 1.161) a subgroup of 96 boys was selected whose behavior had been assessed repeatedly by different informants from age 12 to 21 years, and who had provided multiple T samples over these years of assessment. On the whole, a decrease in aggressive and delinquent behavior was observed in a period in which T rises dramatically. Boys who developed a criminal record, had higher T levels at age 16. In addition, positive associations were observed between T and proactive and reactive aggression and self-reported delinquent behavior. Over the pubertal years different forms of aggressive and delinquent behavior were positively related to T, which may indicate that specific positive links are dependent on the social setting in which this relationship is assessed.