The quality of a student-athlete’s experience can be a product of the services provided by their sponsoring sport organization. In an attempt to improve the student-athlete experience, this study was positioned to examine how collegiate sport services could use academic psychological capital (PsyCap) and student-athlete engagement to promote school satisfaction and psychological well-being. A total of 248 National Collegiate Athletic Association Division I student-athletes participated in this study. Results indicated that academic classification moderated academic PsyCap’s influence on engagement. In addition, the academic PsyCap of the student-athletes positively influenced school satisfaction and psychological well-being, but student-athlete engagement fully mediated the relationship between academic PsyCap and psychological well-being. This empirical evidence provides new knowledge on the relationships among student-athletes’ motivational cognitive constructs, educational engagement, school satisfaction, and psychological well-being in the context of highly competitive collegiate sports. Theoretical and practical implications are discussed, including incorporating the results with services provided to student-athletes.