Purpose: The main purpose of this study was to explore direct and indirect relationships between Leadership and Student Citizenship Outcomes in Cyprus middle schools. In the case of indirect effects the mediating role of School Academic Optimism and Instructional Quality was examined. Method: The specific study adopted a value-added quantitative design. Student achievement data were collected at the beginning and end of the term during which the subject of Citizenship Education was taught. Students also provided data about the quality of instruction, whereas teachers provided data about leadership and school academic optimism. Overall, a multistage sample of 20 middle schools, 114 classes, and 1,596 students participated in the current study. Multilevel modelling and single-level regression techniques were used to identify the relationships between the main variables of this study. Findings: A number of contextual student variables and one classroom variable were found to have a direct effect on citizenship outcomes. Neither School Leadership nor School Academic Optimism were found to have any direct or indirect effect. However, school leadership, along with a number of contextual variables, was found to have statistically significant effects on School Academic Optimism. Implications: The findings highlight the importance of the learning domain when searching for effectiveness factors at the classroom and school level. It is suggested that the subject of citizenship education is upgraded and principals as well as teachers are substantially supported to promote the subject goals.