The core purpose of school leadership is to provide leadership and management in all areas of the school to enable the creation and support of conditions under which high quality teaching and learning can take place and which can promote the highest possible standards of learner achievement. This study aimed to examine the roles of the school principals in monitoring teaching and learning in inner-city and township secondary schools in the Gauteng province. The study used a case study research design in which one inner-city and township secondary schools were purposely selected as cases for the study. The school principals, deputy school principals, heads of departments and educators were observed over a period of fourteen days in each school after which were interviewed. Both the observation and interview protocols were piloted. All interviews were tape recorded and confidentiality was assured. Interviews were transcribed and analysed through content analysis (Strauss1987).Emerging themes were used to create a comparative data set across the stakeholders’ content analysis. The analyses were then triangulated as a means of establishing the trustworthiness of the accounts. Observations and questions focussed upon the roles of the school principal in monitoring teaching and learning with reference to the school curriculum, the tools school principals use in monitoring teaching and learning and how school principals monitor teaching and learning in such schooling contexts. They indicate that the role of school principals as instructional leaders in monitoring teaching and learning is supervision which involves leadership roles in educator professional development, curriculum supervision, collegiality, care and response. They not only indicate the complex contextual roles of school principals in monitoring teaching and learning in the challenging circumstances in the inner-city and township secondary schools, but the mechanisms school principals use to monitor teaching and learning in such contexts. School principals minimally participate in the monitoring of teaching and learning and rely on feedback from classroom observations and learner data collected by the deputy school principals’, heads of departments/ subject heads and class educators to monitor learner performances in the schools.