The Congregation of Holy Cross has been working on evangelization and education in Bangladesh for more than 160 years. However, over the years particularly from 1947 to 2017, there have been many changes – internal and external – to Holy Cross itself and the socio-political, and educational context of Bangladesh. Thus, this study addresses how the educational mission of Holy Cross has responded to the changes, and how those changes have shaped their educational mission in Bangladesh. The study took place in a historical context by following the historical case (multiple cases) study method. This study was based primarily on examination of written documents and field work involving oral history interviews. The study found that Holy Cross education had gone through significant changes because of political and educational shifts in Bangladesh. As their educational missions were formulated, to some extent, in dialogue with governments, the study showed that with regards to educational policies and strategies Holy Cross had different approaches from the government practices. The study illustrates that they are quite successful in missions of – “raising up native clergies”- and establishing a local church. The thesis also argues that they had distinctive educational aims as part of an elite education in both English and Bengali medium, and through primary and secondary education in the villages. While the former was primarily motivated by the idea of -“diffusion of Christian ideals”- and the latter aimed at empowering the Catholics.