The purpose of this case study is to offer reflections for both applied researchers and practitioners on our experiences of investigating coaching behaviors during the COVID-19 pandemic. The case is based on the delivery of remote, online tennis coaching sessions to children over a period of 3 weeks. Questionnaire, observation, and focus group data were collected from tennis players, coaches, and parents/guardians. Analyses revealed similarities and differences with previous investigations measuring coaching behaviors, as well as the perceived effectiveness of sports coaching in an online environment. Novel insights and recommendations for applied researchers and practitioners in sport and exercise psychology are highlighted, including the importance of staying connected during the pandemic, keeping players and parents motivated, and creativity. The authors consider the context of conducting a case study into coaching behaviors during the COVID-19 pandemic itself, and conclude by providing reflections on our case study within the case study of COVID-19. These include enhanced communication (as it was easier to connect with each other), the nature of the online delivery improving presession preparation, and the research process being relatively more straightforward to implement, all due to barriers being removed as a direct result of COVID-19 quarantine, stay-at-home restrictions.