The focus of the research was to explore male and female principals’ views of discipline and discipline strategies they employ for maintaining discipline in schools. The study also attempted to answer whether the gender of the principal makes any difference in discipline management or not. Qualitative investigation guided the design of the study. The study sample comprised two secondary school principals (one male and one female) from private secondary schools in Karachi, Pakistan. They were selected through the mode of purposive sampling. Empirical data was collected by the means of semi-structured interviews, observation through shadowing and document analysis. The data was analysed in accordance with accepted procedures such as transcribing the data and coding it into themes and sub-themes as they emerged from the data. The results indicated the gendered attitude of the principals in discipline management. Both principals consider discipline as a source to maintain sex segregation in the entire school setting. Furthermore, the study revealed that boys receive corporal punishment more frequently in the male principal’s school, because he perceives that boys are physically stronger than girls. Moreover, it was found that the female principal focused on caring, understanding, collaboration, involvement and human proximity as compared to the male head teacher who was assertive in the discipline management. Over all, it was revealed that principals’ strategies of disciplining students are also guided by their personal experiences and socio-economic situation and the cultural practices of the pupils’ parents. The study recommends that both schools need to adopt constructive strategies and incorporate the gender perspective into the discipline policy. Since this study is one of the few researches done in the field in Pakistan it is therefore expected to make a contribution to the gender studies done so far in this context.