Abstract: One of the first significant futuristic concepts concerning the subsequent fate of the Western European civilization and its relationship with other cultures and civilization that emerged in the early XX century are the well-known concepts of O. Spengler and A. Toynbee, interpreted in the fundamental philosophical-theoretical works “The Decline of the West” and “A Study of History”. Despite the theoretical depth and high level of originality of these works, many of the positions still carry a polemical character. The nature of current relationship between West and East in many aspects is defined by the globalization process, which in accordance with the logic of development of the human kind leads to the creation of a universal world economic and financial system that, however, due to a number of reasons escalates the previously existed and generates the new obstinate contradictions, part of which have civilizational roots or at least civilizational specificity. This resulted in origination of diverse concepts; some of them of futuristic character, or in other words, structure and substantiate the future world view in the nearest historical perspective, as well as relatively remote. The strong majority of modern peoples currently experiences the significant cultural transformations that concern its foundations, and will only increase in the future that undoubtedly requires their scientific-theoretical contemplation and assessment. This article is an attempt to comprehend the historical transformation of the West, utilizing the views of O. Spengler and A. Toynbee.