This dissertation focuses on John Dewey’s experience in modern China by exploring educational encounters between Dewey and the five Chinese scholars (Hu Shih, Liang Shuming, Tao Xingzhi, Guo Bingwen, and Jiang Menglin). The main purpose of my study is an attempt to answers an important question: What motivated Dewey’s Chinese students to introduce Dewey’s educational thought to China? Part of an answer is derived by examining a more central question: How did Dewey’s Chinese devotees find philosophical motivation from their Confucian education and Western learning in order to entertain Dewey’s educational thought? By utilizing Jane Roland Martin’s educational theory of encounter as a theoretical framework, this study illuminates the cross-cultural philosophical dynamic that took place between Dewey and his Chinese students. Therefore, I wish to borrow the concepts of “cultural stock” and “individual capacities” from Martin’s theory to understand an encounter between Dewey’s pragmatism and Confucianism during the May Fourth era. Simultaneously, my study also employs Martin’s notion of “double-entry cultural bookkeeping” to analyze how Dewey’s Chinese followers retained “the cultural asset” from Confucian education and Western learning, while removing “cultural liability” from both. According to the finding of this study, Dewey’s Chinese students tried to adopt, transfers and apply Dewey’s pragmatism into Chinese reality mostly because they were eager to find a “miraculous medicine” that would supposedly cure an ill within Chinese society. In other words, Dewey’s pragmatism was very compatible with his Chinese students’ cultural psychology stemming from Confucian educational experience.