The Tōa Dōbun Gakuin University was established in Nanjing in 1900 by the Japan Tōa Dōbunkai for training China experts, and was moved to Shanghai in the same year. It was funded largely by government grants, and was closed in September 1945, one month after the surrender of Japan. During the 45 years of its existence, it had educated 4,368 students, trained many experts in academic, diplomatic, media, and business fields. However, from the Chinese perspective, they were just vanguards of invasion. Among them, there were 30 students from Taiwan; three of them enrolled in the Chinese division of the University in 1920 using forged identities as natives of Fujian and Guangdong. Despite some research done, there is still much room for more in-depth exploration. With reference to documents related to the University from Diplomatic Archives of the Ministry of Foreign Affairs of Japan, passport lists, histories of universities, and records of alumni associations, this paper first describes the history of the University, then explores why Taiwanese students enrolled in the University, and traces their study experiences and careers after graduation. More detailed discussion is given to three students, namely Chen Hsin-tso from Taichung who later served in Guangdong as vice consul of Japan, Peng Sheng-mu from Miaoli who became the deputy division head of the Nanjing Office of the Bureau of Investigation and Statistics, and Wang Hong from Lukang who became a professor of Japanese literature at the Shanghai International Studies University. Though all from the same University, they developed distinct career paths. This research on Taiwanese students of the Tōa Dōbun Gakuin University complements earlier study on Taiwanese graduates from the Waseda University and Nara Women's Normal University, providing a more comprehensive picture in the history of education of Taiwanese studying overseas.