Middle way is an essential idea in Buddhism. The process of history, and geographical differences have led to many interpretations and extending the discussion. This article explores the relationship between the Middle Way thought of Venerable Master Hsing Yun ( VMHY ) and the thought in light of “the Vimalakirti Sutra”(“VS”). As an explanation of Buddhist doctrines and response to the solitary-style of practice, VMHY proposes the idea of Engaged Buddhism, combining Buddhist Practice with daily life. The process of adapting to the modern developments of society, illustrates the characteristics of Middle Way practice, its salient truths as well as the way to liberation. Meanwhile Buddha explained, “Four Noble Truths”, also revealing Middle Way thought behind. Thus, the Middle Way interpretation can be divided into four levels : (1) the cognitive level: explain the idea of getting rid of persistence of feeling on bliss and suffering. (2) the practical level : means the religious practices of the Eightfold Path. (3) the functional level : through the practice can eliminate greed, hatred, and delusion ( ignorance ). (4) the enlightened level : completely transcend the suffering, and being enlightened. “The Vimalakirti Sutra”, also known as “Acintya-Vimoksa Sutra”. Although “VS” never mentioned the “Middle Way”, it is however expressed through the idea of non-duality. As such, this article investigate the Non-duality tenet, it is found that the idea which is not only a philosophical postulation, but also a mean of liberation from dichotomy (kind of enlightenment) through the practice, and “Vimalakirti’s silence without speech” show that the real enlightenment can’t be stated by the linguistic speech . After Buddhism transcended India and arrived in China, it was Sinicized in the face of a rich profound culture, which had a different framework of thought from its own; ad a result, Buddhism had developed new forms of religious praxis. Nowadays, VMHY propagates Humanistic Buddhism thought through the ideas of daily life cultivation; he transcends the traditional paradox of daily life and practice, illuminating the Middle Way life that Shakyamuni Buddha advocated. Through the three ways of expression: disapproving, affirming, and circular thinking, one finds similarities in the interpretation of Middle Way thought between VMHY and that of the Vimalakirti Sutra. For example: Firstly, both disagree with the solitary-style practice, and world-escaping behavior, eliminate the persisting in dharma through the contractive way of thinking. Secondly, both indirectly disapprove the twofold opposition, but employing transcendental concepts to encompass opposition as a means of preventing polarization. Thirdly, both employ circular thinking to address more effect ways for transcending dichotomy. This study concludes that through the three ways of expressing, one can identify the Middle way thought of VMHY and “VS” as well as highlight the wisdom behind their application.