This study aimed to identify different groups of adolescents who have distinct profiles based upon their perceptions of interpersonal and activity-based dimensions of the sport environment. A sample of 310 adolescents from Eastern Canada (Mage = 14.69 ± 1.60 years; 54.8% girls) completed questionnaires assessing selected interpersonal, activity-based, demographic and sport-specific variables. Using TwoStep Cluster Analysis, we identified three groupings of adolescent sport participants. Consistent with the literature, we labeled these groups ‘negative context,’ ‘positive context,’ and ‘complex context,’ respectively. As expected, participants in the last two groups reported greater enjoyment, perceived competence, and commitment to sport. Further, participants in the ‘complex context’ group showed the highest levels of sport commitment. We draw on insights from Csikszentmihalyi's theory of complexity and relational conceptions of compensation and resilience to interpret the findings, and offer an alternative account of contextual conditions suitable for adolescents involved in competitive sport.