In this study path analysis was used to examine eight different aspects of Japanese and Australian students’ experiences of school life in relation to their effect on adaptation to school. Adaptation was conceptualized in terms of enjoyment of school, feelings of belonging to school, and relationships with other students. Data from over 3000 Australian and over 5000 Japanese students (Years 5-10) were collected to test two country specific models of adaptation to school. A questionnaire was developed collaboratively by the authors to examine issues of common concern in both countries. Issues that related to the impact on adaptation to school of stress and support, namely, family, teachers, peers, and school work, as well as bullying, were of particular interest. Lack of support and the effect of stress were found to affect adaptation to school negatively, especially among high school students in Australia and Japan. The finding of a strong relationship between bullying others and victimization is discussed in the paper. Finally, the differences and similarities between Japanese and Australian students’ perceptions of school are extrapolated.