Students engagement with school is a concern of the educational community, research and policy makers. It has been conceptualized as a multidimensional construct conditioned by several individual and contextual factors, namely personal, family, social and academic variables. Regarding academic variables, school retention is a controversial option, that influences the way students engage with school. Many studies have examined the impact of retention on school performance. Less attention has been directed to the implications of retention on students' school engagement, particularly in its cognitive and psychological domains. The objectives of this study were to describe the cognitive and psychological dimensions of school engagement in students from 4th, 6th and 9th grades, and to analyze the influence of retention in the engagement with school. A total of 986 students, who attended elementary and middle school, participated in this study. This study contributed to the research on school engagement and retention, adding empirical evidence to this subject, and suggesting that retaining students may contribute to the decrease of engagement with school throughout the academic journey. These results may have implications for educational policies and psychological practice, especially highlighting the belief that in school no child should be left behind.