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This study applies Agnew’s general strain theory (GST) to examine the relationship between criminal victimization and offending. While generally well established by prior research, there has been limited research studying whether this relationship is affected by the community contexts in which it takes place. To address this relatively neglected issue in GST research, we focus on two different types of victimization, experienced and anticipated, to see whether they have differential relationships with different types of negative emotions and offending as GST would predict. It is hypothesized that experienced victimization is more likely to be positively associated with violent and property delinquency, mainly via anger, than drug use. Anticipated victimization, however, is more likely to be positively related to drug use, primarily via depression and anxiety, than violent and property delinquency. Also, we examine two different types of contextual variables: collective efficacy and community disorder. We hypothesize collective efficacy to decrease the victimization-offending relationships; and community disorder – specifically, neighborhood disorder and, to a lesser extent, school-surrounding disorder – to increase these relationships. To test these hypotheses, we analyze panel data collected from Korean adolescents. Implications for theory and future research are also discussed.