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 socioeconomic and cultural contexts vary greatly. This study thus compared how the conceptualization of inclusive education and elements that affected inclusive education in Guam and Hong Kong where vastly different socioeconomic, and cultural contexts were present. A qualitative approach of interviewing school leaders was adopted to permit an in-depth understanding of these contexts. Findings affirmed the significance of contextual analysis in understanding the conceptualization and practices of inclusive education in the two study sites. It was concluded that more cross-national qualitative studies are needed to examine contextual factors for meaningful understandings of school reform policies, practices, and challenges.