This paper presents results from the study of gambling behaviors in a representative sample of Cypriot high-school students. The aim of the study was to ascertain epidemiology of adolescent online gambling in Cyprus and possible correlates. The sample consisted of 2,684 students (48.5 % boys, 51.5 % girls) from the first grades of junior (Gymnasium) and senior (Lyceum) high school. Our results indicate that gamblers presented with lower school achievement and related expectations while scoring consistently higher on measures of Internet addiction, parental bonding and psychopathology. Discriminant analysis revealed two profiles which explained the most variance in gambling behavior; the first profile that corresponded to more explained variance was the student with higher psychopathology, less prosocial behavior, higher Internet addiction score with higher frequencies of online activities and moderate levels of truancy and lower expectation of school achievement. The second profile was that of a student who reported less psychopathology, more prosocial behavior, less involvement with the Internet in general but skipped classes more and his prospects on finishing high school were even slimmer. These results will be utilized in the design of a comprehensive prevention program in an effort to combat online addictive behaviors.