Chinese (martial arts) and Western (sports) cultures started their encounter and fusion under the specific historical atmospheres of China’s new culture movement and the debate on ‘Chinese essence and Western practice’ or ‘Western essence and Chinese practice’. This paper analyzes the Chin Woo Athletic Federation as a case study, aiming to explore the operation of its dual-track physical training system and to understand how this organisation positioned, expanded, and perpetuated its influence through media in the turbulent Chinese society. This study analyzes newspapers from late Qing and Republican China from the period between the 1910s and 1930s. The results reveal that the thinking and practice of Chin Woo’s dual-track training system constructed an image of ‘interoperability of Chinese and Western sports’ based on the words and photos in the press and embodied its brand position of cultivating healthy citizens. Chin Woo’s practice model included setting up special Chinese martial arts and Western sports departments and sending members to the regional, Far East, and Olympic games. As such, the Chin Woo Athletic Federation presents an appropriate example of the cultural flow of Oriental and Western sports.