Professional sport teams allocate a significant amount of time and financial resources to corporate community involvement programs such as urban youth sport programs because of their importance in positive youth development. Research documenting the association between sport participation and educational outcomes has mainly focused on in-school extracurricular activities and only examined academic achievement. Therefore, it is imperative that researchers evaluate broader academic outcomes of youth sport participants in out-of school extracurricular programs. One mechanism through which these effects can be implemented and evaluated is through community-based participatory research. Using this highly collaborative strategy, our research team worked with administrators from a professional sports team, local parks and recreation departments, as well as youth baseball coaches and their athletes. The aim of this case study was to examine the relation between participating in a professional sport team’s youth baseball program and youth educational achievement, school engagement, and how various demographic factors affect this relation. Participants were asked to complete questionnaires addressing these areas before the beginning of their baseball season and again 6 months later, applying a repeated-measures design. Descriptive and inferential statistics were calculated to address our research questions. In this case study, we outline the community-based participatory research approach to conducting research, highlight several of the challenges we encountered, and reflect on the lessons learned throughout this process.