This article examines the historical backdrop to the involvement of teaching Sisters in convent schooling for girls in India and the Islamic Republic of Pakistan, since the late nineteenth century. It then explores how, as a consequence of a range of social changes, leadership in convent schools has changed in both countries, across the twentieth century. The Irish Sisters who founded and established these schools commenced "passing the baton" of convent school leadership to Indian and Pakistani women. The article draws on interviews to examine ways in which successive generations of women in the study refer to the legacy of the past, and the issue of women in education leadership.