Enormous variation exists among nations and regions in their inclusive education provisions. In addition to comparisons based on policy documents and figures, in-depth and contextually grounded comparative studies involving qualitative data based on stakeholder experiences are needed, especially between western and Asian regions or nations where socio-economic and cultural contexts vary greatly. This article examined and compared how the conceptualization of inclusive education and elements that affected school leaders' decisions to participate in inclusive education in Guam and Hong Kong where vastly different socio-economic and cultural contexts were present. An interpretive qualitative approach of interviewing school leaders was adopted to permit an in-depth understanding of these contexts. Findings revealed that the legislation-based versus the cultural heritage of Confucianism and the geographical location versus the elite education system of Guam and Hong Kong were key contexts affecting conceptualizations and challenges in the two regions. Large scale cross-national qualitative studies are called for to examine contextual factors from other key stakeholders, to give meaning to statistical figures and policy documents, and to offer more meaningful interpretation of the relationship between national contexts and inclusive education provisions.