Socrates and Confucius constitute roots of western and eastern civilization respectively, as well as represent very different cultural values and educational traditions. Because of the very limited existing literature on the study of their educational philosophies, this paper is devoted to a comparative study of their educational philosophies, attempting to examine their historical and cultural contexts and unravel their implications on the current educational practices. The method employed in the study is hermeneutics, or interpretation of the literary texts. At the same time, the study is also cross-cultural in nature. Both of the philosophers lived around 4-5th century B.C.E., but there were huge differences in the social and cultural environments in which they lived. Different cultural and social factors in ancient Greece and China led to differences in Socratic and Confucian approaches to learning. In this paper, similarities and differences in Socratic and Confucian educational philosophy have been examined from the perspectives of the aim of education, the content of education, the teaching process and the nature of education. It is argued that the epistemological differences of the two philosophers were interwoven with their respective cultural values. Individualistic and rationalist traits were embedded in Socrates’ education, while Confucius’ teaching was distinctively marked with collective and intuitive characteristics. Their thoughts were the product of their own culture, and at the same time, the thoughts of philosophers also left deep impacts on the development of each culture. Their philosophies of education impacted not only their disciples, but Western and Chinese educational practice as a whole. It has been found that the Socratic traits of individualism and rationality are embedded in Western educational practice, while the Confucian heritage and the collective-intuitive tradition in the Chinese education. The current study is significant in helping readers gain a better understanding of the philosophers from a cultural perspective. In the same way, educational practice must be understood from multiple perspectives. It is suggested that cultural contexts should always be taken into consideration when studying a particular teaching or learning style. In spite of its limitations, the researcher hopes that the study will help western and Chinese teachers and learners gain a better understanding of one another.