Sport-for-development (SFD) is a growing phenomenon involving engagement in sport activities to achieve international development goals. Kicking AIDS Out is one sport for development initiative that raises HIV/AIDS awareness through sport. Despite sport-for-development’s global prevalence, there is a paucity of literature exploring how activities are selected for use in differing contexts. An occupational perspective can illuminate the selection of activities, sport or otherwise, in sport-for-development programming and the context in which they are implemented. The purpose of the study was to understand how context influences the selection of sport activities in Kicking AIDS Out programs. Thematic analysis was used to guide the secondary analysis of qualitative data gathered with Kicking AIDS Out leaders in Lusaka, Zambia and Port-of-Spain, Trinidad and Tobago. Findings include that leaders strive to balance their activity preferences with those activities seen as feasible and preferential within their physical, socio-historical, and cultural contexts, and that leader’s differing understandings of sport as a development tool influences their selection of activities. To enable a better fit of activities chosen for the particular context and accomplishment of international development goals, sport-for-development programmes might consider how leaders are trained to select such activities.