SRL has been posited to explain student-athletes concurrent success in sport and academics. The purpose of this dissertation was to empirically explore student-athletes’ self-regulated learning (SRL) in and across their academic and sport learning. Three manuscripts addressed two overarching goals: (a) explore the relation between SRL in sports and academics, and (b) explore methods of measuring SRL. First, in McCardle, Jonker, Elferink-Gemser, and Visscher’s (2014) study, competitive youth athletes (N = 215) self-reported on self-regulatory and motivational engagement in sport and academics. Findings revealed a positive relation between SRL in these contexts and more reported engagement of SRL in sports than in school. Second, McCardle (2014) conducted a case study of one student-athlete’s SRL in sport and school. Based on interviews, journals, and video-stimulated recall, the student-athlete demonstrated clear similarities in how he engaged SRL in both contexts. Some differences between sport and academic learning emerged, suggesting potential differences in support for SRL in the two contexts. This paper explored potential of qualitative measures of SRL in by combining multiple qualitative measures of SRL to create SRL profiles in sport and academics. Third, McCardle and Hadwin (2015) explored use of two types of self-reports considered event measures of SRL as they focused on single learning episodes (N = 263): (a) a quantitative questionnaire measure of SRL related to one study episode for an exam, and (b) a qualitative diary related to setting and attainment of one study goal. Contrasting these two methods revealed varying degrees of similarities in students’ self-reports. Together, this research highlights the potential of transfer of SRL across sport and academic domains and the importance of appropriate measures to capture event- and aptitude-based SRL and suggests several avenues for future research. To conclude, I suggest Winne and Hadwin’s (1998) model of SRL serve as a framework for researching SRL transfer with a focus on conditions. New research in transfer has potential for contributing to SRL research on how learners draw on previous regulatory experiences to adapt to new challenges.