E-learning quickly became a crucial tool for universities and other higher education institutions during the global COVID-19 pandemic. The field of sport and physical education (PE) was no exception. However, though there is considerable growth in digital technologies in sport or physical education, we have very little evidence about the use and outcomes of these technologies. Thus, this study aims to document how e-learning technologies and pedagogical approaches were employed in the field of sport, the challenges and successes associated with these approaches, and potential avenues for improvement. To do so, a total of 27 responses were collected with two online qualitative surveys, one respectively for students (n = 15) and one for teachers (n = 12). Structured follow-up interviews with four students and one additional teacher were conducted to verify and deepen the responses. The findings show that interaction and variety were critical components of successful online learning. However, teachers reported difficulties motivating students, especially if no visual connection was present. Ultimately, even with innovation, variety, and interaction, sport and physical education’s practical and social nature does not fully translate to the online setting. Thus, we conclude by proposing potential avenues for practice and research to respond to the challenges documented here.