This work provides an analysis of the two inter-related processes of Buddhist meditation, samatha and vipassanā. Despite their frequent appearance in the Buddhist canonical and commentarial texts, most scholars have not settled the exact role of samatha and vipassanā in the path of enlightenment. They continue to remain divided over the question as to how samatha and vipassanā are related. This research contributes to the eventual resolution of this question for the Buddhist presentation of the way to liberation. The determination will focus on the clarification of samatha, vipassanā, and their collaboration. The clarification of samatha begins with its etymological study as well as the detailed examination of the principle equivalent term, ‘samādhi.’ Its perspective of important set of concentrative attainments, namely, the jhānas will be investigated covering three major areas: the general characteristics of the term ‘jhāna,’ the specific characteristics of each jhāna state and the potentiality of subject of concentration for the jhāna attainments. This investigation of jhānas focuses on their relationship with vipassanā contemplation and Buddhist ultimate goal in reference to the mental quality rather than meditative exercise. The critical analysis of vipassanā is based on two inquiries: the development of vipassanā, and its advantage. The first inquiry is to explore the etymological characteristic of the term ‘vipassanā.’ And then the commencement of vipassanā will be discussed in relation to the complementary process which is samatha. The second inquiry is to examine how the process of vipassanā operates in order to overcome the mental defilements. The evaluation of the relation between samatha and vipassanā will be performed to understand the path of enlightenment. This section aims to clarify the issue of whether or not samatha needs to be strengthened during the process of vipassanā and how they work together in order to nullify all cankers.