Student-athletes are at risk of impaired well-being due to the demands of combining a career in both school and sport. Moreover, negative and positive role interactions (i.e., sport-school conflicts and enrichments) may play an important role in student-athletes' well-being. Therefore, the purpose of the present study was to examine the week-level relationships between role interactions and four contextual well-being indicators among student-athletes. Thirty-one student-athletes (15 females, 16 males) completed a weekly survey across 5 months resulting in 331 observations on their perceived conflicts and enrichments between student and athlete roles, sport-and school-related stress, and sport-and school-related satisfaction. Negative and positive role interactions predicted between 35% and 51% of the week-level variance in contextual well-being. Consistent with our hypotheses, sport-school conflicts positively predicted sport-and school-related stress. Sport-to-school conflict negatively predicted school-related satisfaction, whereas school-to-sport conflict negatively predicted sport-related satisfaction. Sport-to-school enrichment negatively predicted sport-related stress and positively predicted sport-related satisfaction, whereas school-to-sport enrichment negatively predicted school-related stress and positively predicted school-related satisfaction. The results of this study help to better understand student-athlete well-being. They show that contextual stress and satisfaction vary significantly at the week level among student-athletes and that sportschool role interactions could predict these variables.