The intriguing maneuvering and distinguished styles of traditional cycling combined with the growth of eCycling as an eSport share an intriguing array of similarities as well as new ways of looking at cycling through competitive sports environments. It is an important discussion, associated with distinguishing the pathways and opportunities available to cycling stakeholders as they experience and engage in their sport, including the virtual participation in eCycling and inclusive competitive options, ever increase and evolve. Virtual cycling is a subset of the eSports genre and offers cycling stakeholders an alternative and a complement to traditional competitive cycling. In 2019, the international federation responsible for cycling globally, the Union Cycliste Internationale (UCI), who acts as the steward and regulator for global cycling activities recognized eCycling as a legitimate discipline and authorized a recognized virtual eSports World Championships. The origins of video game eSports, marketing tactics, and health outcomes are also discussed in the chapter.