Lickona (2004) states that "of all the school's extracurricular activities, sports typically have the greatest impact on the school's moral culture, for good or for ill. Deliberate strategies are needed to make sport a character-building rather than a character-eroding experience" (p. 74). In Singapore, the Ministry of Education states that participation in CCA (Extracurricular Activities) develops character. With limited evidence to support this claim, this study aims to investigate the possibilities of positive character development among the participants of a football CCA program with a structured curriculum which includes scaffolding through a training journal, and to document its outcomes. This is a year-round programme whereby students in a secondary school participate in practices, friendly games and Inter-School competitions. Participants use a training journal to record and share their learning experience. The footballers met once monthly, with seniors (mentor leaders) leading a discussion on related values found in John Wooden's Pyramid of Success (2008). The mentor leaders are also involved in coaching a group of primary school pupils in football. The data will be collected in a secondary school in Singapore. 45 participants between 12-16 years old are involved in this study, which involves both quantitative and qualitative data collection. Participants will respond to a questionnaire package pre and post programme. First, the Perceived Motivational Climate in Sport Questionnaire-2 to examine the team climate; second, the Prosocial and Antisocial Behaviours in Football Questionnaire-3 to examine moral behavior during a football season; third, the Task and Ego Orientation in Sport Questionnaire to assess the task and ego orientations in sport context. Participants who show significant differences in task orientation score will be selected for an in-depth interview. The interview will seek to find out how the motivational climate affects the motivation orientation, their experiences and the skills from the journal that were applicable in life. It is expected that participants with high task-oriented score and greater frequency of engagement in the CCA program will reap positive developments in this programme. The results of this study are important in order to provide documented evidence of the impact of a structured programme on the motivational climate of a CCA, and therefore on youths' character development. It is hoped the programme will be useful for coaches or teachers-in-charge of their sports CCAs, to create a more task-oriented motivational climate to foster character development.