The overarching purpose of this study is to examine the prospects of school leadership for the development of intercultural education. The article focuses on the ways in which Greek-Cypriot headteachers conceptualize: diversity and intercultural education; and their school leadership roles in culturally diverse settings. To this extent, interviews were carried out with the headteachers of 20 primary schools, which presented high concentrations of immigrant students. In general, two main approaches concerning intercultural education were identified: cultural-deprivation and cultural-celebration. Headteachers, who fostered assimilation in their schools, adopted a transactional leadership style the goal of which was ‘unobstructed’ and ‘unproblematic’ operation of their schools. Conversely, headteachers, who ‘celebrated’ diversity in their schools, opted for the transformation of their school cultures by promoting immigrant parental involvement and community liaison. Nonetheless, there was a third category of headteachers, who held container concepts of diversity, pertaining to both cultural-deficit and cultural-celebration approaches. These headteachers proclaimed the transformation of their schools to accommodate diversity by creating collaborative networks in their schools. However, such suggestions seemed to be rhetorical, while in practice they seemed to seek assimilation.