Drawing primarily on the concepts of self-control, differential association, and social bond, this paper explores delinquent and risk behaviour among high school students in a Canadian prairie city. A total of 262 students attending 14 high schools participated in a self-administered questionnaire survey. The results demonstrated that a notable number of students engaged in various risk (e.g., drinking, unprotected sex, and smoking) and delinquent (e.g., use of illegal substance, theft, and vandalism) behaviour. Multiple ordinary least-squares regression analysis revealed that males, older students, and those who had parents with a lower level of education, considered religion to be less important, scored lower on the self-control scale, indicated having more close friends who used illegal drugs, and reported having been a victim of violent or property crime were shown to have a greater likelihood of risk behaviour involvement. On the other hand, male respondents and those who scored lower on the self-control scale, associated with individuals who used illegal drugs, and reported having been a victim of violent or property crime were found to be significantly more likely to engage in delinquent behaviour. Policy implications of these results for institutional interventions are briefly discussed.