The "Taiwan Educational Association Magazine Chinese version" was an important press in the Japanese colonial period of Taiwan regarding the interrelations between Japan and Taiwan in Classical Chinese. It contained two main areas of classical Chinese poetry and essays, and modern educational enlightenment. This paper analyzes the two areas by focusing on the magazine during the Meiji period. It asks questions as follows: How is the interrelation shaped by introducing classical Chinese knowledge and literary works? What kind of political and cultural ideas lie behind knowledge dissemination and literary network? The works of classical Chinese decipher a complicated picture in which two sides of colonial governance can be found. On the one hand, Taiwanese were convinced by the Japanese editors in charge of editing and writing, who showed off their refined capability of classical Chinese lyrics on purpose. On the other hand, classical Chinese, particularly essays, was used for colonial ruling by promoting modernity. What is more interesting is that the chief-editor, Mitsuya Daigoro, intended to transform traditional Taiwanese customs by adapting Liang, Qi-Chao's essays published in Japan. The paper provides a cultural reading by looking into cultural and political phenomena in the magazine regarding complicated relations between Taiwan, China and Japan. The paper starts with reviewing current relevant research work and discussing the formation and objectives of the magazine. It continues to focus on two parts of interrelation of classical Chinese literary works and modern knowledge dissemination. The former includes three aspects: 1. The dissemination and resources of classical Chinese knowledge, 2. Two sides of the interrelation: from assimilation to appreciation, 3. The skill demonstation of classical Chinese and its intention by Japanese in Taiwan. The latter entitled "the introduction and complex of modern intellectual enlightenment includes 1. The introduction of colonial modernity, 2. Promoted "pros and cons," 3. The adaption of the essay "On forbidding early marriage" by Liang, Qi-chao.