Background As a result of the coronavirus disease 2019 (COVID-19) pandemic, graduate medical education, along with most of daily life, was disrupted. The goal of this study was to explore the experiences of fellows in primary care/medical sports medicine (MSM) and view the changes made to training programs through their eyes. Methodology A questionnaire was developed to collect qualitative and quantitative data regarding the fellow's experiences in training from March to June 2020. Fellows on the American Medical Society for Sports Medicine list of current Sports Medicine Fellows in the United States and Canada were invited to participate. Of the 329 invited, 90 (27.4%) fellows returned questionnaires. Results MSM fellows highlighted positive adaptations as well as losses to their educational programs related to the pandemic. The biggest gain reported was additional learning time, and the greatest loss was to sports and event coverage. Most fellows reported attending collaborative sessions, and they noted an increase in didactics compared to pre-pandemic levels. The largest losses were noted in event coverage and training room exposures, with smaller declines in ultrasounds, procedures, and research experiences. They also described challenges, including changing clinical roles, managing social isolation and boredom, and balancing work and family responsibilities. Conclusions Fellows identified gains, losses, and challenges due to pandemic-related changes to their fellowship programs. Fellowship directors and educators in different fields can use this understanding of the fellows' experiences to build on current resources, further develop collaborative efforts, create new educational opportunities, and provide additional support for fellow learning.