Character education programs are mission-aligned with the positive youth development (PYD) perspective, which, in research with American youth suggests that intentional self-regulation (ISR) develops through mutually beneficial interactions between youth and their environment. Cross-cultural studies of Western youth suggest an adolescence-specific ISR process may exist. We begin to extend this work to assess the relationship between ISR and positive development in young Scottish adolescents (approximately 7th grade, N = 82; 50% male), a previously unexamined group. ISR was correlated with the Five Cs of PYD and OLS regression analyses demonstrated that ISR predicted two of the Five Cs: Character and Connection. We discuss implications for youth development programs of the findings that ISR and some indices of PYD were linked in a sample of Scottish youth.