In this paper we present data from a cross-sectional study on cyberbullying experiences and cyberbullying perpetration in the Republic of Cyprus. Data were collected from a representative sample of the adolescent student population of the first and fourth grades of high school. Total sample was 2684 students, 48.5% of them male and 51.5% female. Research material included extended demographics, a detailed questionnaire on Internet activities, the Parental Bonding Index (PBI) and the Strengths and Difficulties Questionnaire (SDQ). We compared the results on psychometry for those students who did not report being bullied or having bullied others with those who were bullied, those who bullied others and those who were both sufferers and perpetrators of cyberbullying. Those students who reported being both victims and perpetrators tended to show similar or higher dysfunction than those students who only perpetrated cyberbullying. High maternal and paternal protection in combination with low maternal and paternal care (‘affectionless control’ parenting style) was associated with perpetrating cyberbullying, either with or without any experience of oneself being bullied as well. Results support a hypothesis that the perpetration of cyberbullying is associated with inefficient parenting styles. They also point to the existence of significant emotional symptoms for the involved adolescents and also general conduct problems, hyperactivity, peer problems and antisocial tendencies. It is important to note that perpetrators of cyberbullying were in most cases victims themselves at some point in time.