Using historical narratives and a qualitative research approach, this article aims to understand how competitive gaming has established its relationship with sport and the Olympics in the past five decades, and further discusses the obstacles and challenges for esports’ Olympic inclusion. In the 1970s and 1980s, game manufacturers and publishers, consciously or unconsciously, forged a link between video games, competition and sport. Beginning in the early 2000s, due to its overwhelming popularity, efforts have been made by various organisations to have esports accredited as a full sport. In recent years, sporting governing bodies have started to take esports seriously, and the International Olympic Committee (IOC) has made efforts to incorporate it into the Olympic movement. This article suggests that the IOC must adopt a more open-minded and inclusive approach in order to better understand the esports ecosystem and the young digital generations.