Both School of Hegalianism from the Western philosophy and School of Taoism from the ancient Chinese intellectual schools of thoughts can be unquestionably epitomised as two quintessential, enigmatic schools of dialectics, which to a large degree facilitate the intellectual researchers and scholars within the field of philosophy, humanities, social sciences and so forth to theoretically deconstruct and extrapolate the complex, authentic, objective world system and global human civilisations in a dialectical and synthetic fashion instead of the metaphysical and intuitive perspectives alone. In that regard, the hypothetical questions of 1) whether both Hegalianism and Taoism share certain implicit reciprocal conceptual components that may outweigh their explicitly diametrical diversity owning to the explicit heterogeneity in historical background, social development trajectory, and socioeconomic and politico-economic development pattern between the Agrarian Civilisation and the Oceanic Civilisation in history, and of 2) whether their intellectual thoughts and legacies of dialectics can accurately monitor and predict the infinite occurrence of inter-civilisational, international development issues and human development affairs may at least help to construct a thought-provoking theoretical guideline and framework, which are unquestionably worthy of profound theoretic investigation and empirical analysis. The ultimate purpose of this academic manuscript attempts to dialectically identify and deconstruct certain vital dissimilarities and complementarities between Hegelianism and Taoism and philosophically build a theoretical bridge that interconnects them for the sake of follow-up empirical analysis of their differentiated methodologies. Moreover, this paper seeks to in a dialectical fashion evaluate the availability, applicability and functionality of these two intellectual schools in a context of inter-civilisational and international development, especially pertaining to the underlying themes of global economic crisis and macroeconomic recovery, the unprecedented global climate crisis, and global COVID-19 pandemic with much insufficiency of global sanitation partnership reform and imbalanced means of production. This academic manuscript seeks to itemise and quantify the diverse conceptual components between Hegelianism and Taoism as well as qualitative comments on their potential areas that they might share and develop. Additionally, this paper attempts to undertake hermeneutic retrospectives of their legacies of dialectics and case studies of international, inter-civilisational development issues and human development issues. In a nutshell, on a basis of existential research findings so far, this paper draws preliminary conclusions that the reflexivity of dialectics from Hegelianism and Taoism helps to classify and clarify the implicit dogmatic principles that drive the advancement of global human development, and inter-civilisational development on the grounds of dialectical antithesis as the theoretical guidelines. On the other hand, neither of them can mostly accurately function as a guarantee for maximum prediction and monitoring of world affairs, which necessitates updated data elaboration, comprehensive out-of-box thinking mode, maximum interdisciplinary theoretical breakthroughs and discovery from a maximum dialectical, inter-civilisational perspectives. That can prevent the readers, scholars and researchers from falling into the idealistic solipsism.