This study explores principal-student relationships in a private Montessori to Secondary school in Karachi. The study was contextual which necessitated the design of the study to adopt a qualitative case study paradigm. Observation and interview were the main methods for data collection. The study analyzed the data using grounded theory development approach. The research participants included the principal of the school and nine students from grades 4 to 8. Principal-student relationships at School of Educational Excellence (pseudonym) are in a variety of dimensions. Many of the nuances of these relationships are influenced by such contextual factors, such as principal's beliefs and past experiences, and the stereotypical conceptions about students, such as them being obedient and mannered. These relationships provide different purposes, such as knowledge delivery and controlling student behavior. The Madam' or the Godmother' emerges as the most important person for students in the school. The study also found that the principal deals stringently with students' behavioral issues more so in the case of male students. Principal's perceptions of girl students adopt a stereotypical image as them being obedient and docile. The study finds that the principal's gender becomes significant in principal-student relationships. Furthermore, principal-student relationships are also seen to be influencing other relationships such as principal-parent relationships, principal-teacher relationships and principal-governors relationships. Research literature on principal-student relationships being scanty in Pakistan, the study's findings are significant as they give a qualitative insight into the beliefs and practices of a principal's relationships with students. It is also significant as it highlights the influences of principal-student relationships on students' engagement in learning in the school. This study throws light on how principal and students behave in relation to each other. Also, it adds to our knowledge of how principal and students view themselves in relation to each other in a secondary school, thus contributing to our overall understanding of principal-student relationships in schools in Pakistan. To sum up, this study explores some of the inter- and intra-relationship intricacies, and how they have a bearing on the principal-student relationships.