This work consists of six chapters. The first presents the purpose of the study, research questions, assumptions, and background information. The second presents a reach theoretical framework and literature review relevant to academic underachievement. This includes the bio-ecological theory of human development and other specific theoretical aspects under personal, home, school, and cross-systems levels. The third chapter provides detailed information about the followed research methodology and procedures. The forth chapter presents the results about the associations between academic underachievement and the studied factors under the personal, home, school and cross-systems levels. It also includes the models of the most important factors explaining academic underachievement. The fifth chapter discusses the factors that revealed associated with academic underachievement based on the presented theoretical framework and supported with research literature. The results from the models are also discussed in this chapter. The sixth chapter presents a conclusion about the results and the methodology, as well as, practical recommendations for further research and intervention.