As corporate community initiatives (CCI) in sport are becoming an important dimension of corporate social responsibility, a key issue is evaluating the quality of the processes by which they are delivered and how they are managed. The purpose of this study was to explore the implementation process of a professional sport team’s CCI using program evaluation theory (Chen, 2005). Interviews were conducted with 42 key stakeholders (team executives, partnership implementers, participants, parents, coaches) from one Major League Baseball team’s CCI to understand critical processes involved in CCI implementation and execution. The findings showed concerns in the quality of program implementation with the: 1) the partnership agreement, 2) the ecological context, 3) protocol and implementation, and 4) target population. We propose an iterative model of program evaluation for use in the sport context. We conclude the paper with recommendations for further research in this area and implications for practitioners.