The present study examines the relationship between different roles in cyberbullying behaviors (cyberbullies, cybervictims, cyberbullies-victims, and uninvolved) and self-reported digital piracy. In a region of central Spain, 643 (49.3% females, 50.7% males) students (grades 7–10) completed a number of self-reported measures, including cyberbullying victimization and perpetration, self-reported digital piracy, ethical considerations of digital piracy, time spent on the Internet, and leisure activities related with digital content. The results of a series of hierarchical multiple regression models for the whole sample indicate that cyberbullies and cyberbullies-victims are associated with more reports of digital piracy. Subsequent hierarchical multiple regression analyses, done separately for males and females, indicate that the relationship between cyberbullying and self-reported digital piracy is sustained only for males. The ANCOVA analysis show that, after controlling for gender, self-reported digital piracy and time spent on the Internet, cyberbullies and cyberbullies-victims believe that digital piracy is a more ethically and morally acceptable behavior than victims and uninvolved adolescents believe. The results provide insight into the association between two deviant behaviors.