Sport and physical activity programs have been accepted as a popular approach in reaching out to underserved youth, and delivering educational values and resources (Hartmann, 2003). Don Hellison's Personal and Social Responsibility Model (PSRM) has been widely applied not only in underserved community youth programs, but also for school physical education programs (Hellison, 1995). Most of the PSRM-based program evaluation research, however, has focused on the impact of program participation on participants' changes in school life by examining program participants' changes in school-related outcomes (e.g., office referrals, GPA, reprimands) (Cummings, 1998; Martinek, McLaughlin, & Schilling, 1999). These studies, however, did not consider the complexity of school context in which the application of program goals is expected to occur. In order to facilitate understanding of participants' connection between program experiences and their school lives, the comprehensive understanding of youth program and their school lives are critical. The purpose of this study was to describe the participants' perceived culture of a responsibility-based physical activity program called Project Effort and its participants' school culture. Based on Students' Multiple Worlds Model (Phelan, Davidson, & Yu, 1998), this study examined how the perceived cultural similarities and differences influenced participants' ability to transfer program goals to their school setting. Participants were selected from the pool of Project Effort elementary school club members who also attended Hope Academy. Three fourth graders (two girls, one boy) and two fifth graders (one girl, one boy) participated in the study. This study was conducted through a qualitative case study that included participants' individual interviews, classroom teacher interviews, a program leader interview, and observations of participants' involvement at Project Effort and school. The cross-case analyses results supported that participants' perceived characterizations of Project Effort were centered on the content of Project Effort (e.g., playing sports, learning goals), benefits of Project Effort (e.g., improving grade and behaviors), and atmosphere of Project Effort (e.g., entering the zone of comfort). Participants' perceived characterizations of school were centered on feelings of boredom, lack of freedom, concern for safety, and feelings of anger. In addition, some of the Project Effort values (i.e., respect, self-direction, responsibility) were distorted in the school setting as a way of behavior control. Two Project Effort goals (i.e., self-direction, helping others) were less emphasized in the school setting. The participants' perceived cultural compatibility and differences were related to certain facilitators and barriers of transference of program goals to the school setting.