Despite being the global game, football has never been a popular sport in Taiwan (Republic of China). Instead, baseball, a legacy of Japanese colonization between 1895 and 1945, has fulfilled the role of the nation’s most popular sport. After the Chinese Civil War and the retreat of the Kuomintang to the island, Martial Law was in place for 37 years and civil society was severely suppressed during the period. Despite its marginal status, however, football was appropriated as an extension of the military apparatus. Furthermore, with the assistance of Hong Kong football players, the Republic of China team won gold medals in men’s football at both the 1954 and 1958 Asian Games. Yet, football still failed to take root in Taiwan. From the 1990s onwards, however, there have been football-related interaction between Taiwan and mainland China (PRC). Po-liang Chen, the captain of the Taiwanese national football team and four other national team players, currently play in the PRC with the employment of these Taiwanese players being impacted by the Chinese government’s fluctuating policy towards Taiwan. In such circumstances, the migration of these football players has triggered a bifurcated sense of identity towards China. On the one hand, the Taiwanese people recognize the economic prowess of China and want to seize the opportunities this offers. On the other hand, football fans in Taiwan continue to develop a unique political and cultural identity distinct from their rival. This chapter examines the complex relationship between Taiwan and China through football in different eras to shed light on China’s ambition in relation to the development of football, with particular reference to the implications for Taiwan.