This article is dedicated to the analysis of Turkey-Syria conflict. The is to examine the causes and course of this confrontation from the perspective of historical prerequisites, as well as assess the prospects of further cooperation within the framework of transforming system of international relations and change in the regional balance of powers in the Near East. Detailed analysis is conducted on the policy of the leadership of the Republic of Turkey with regards to Syria since its foundation until the present. Special attention is turned to the Turkey’s current Near East policy, in which Ankara attempts to strengthen its positions in the region, using Syria as a space for implementation of its Neo-Ottoman ideas. The article also reveals a range of problems that impede normalization of the bilateral relations between Turkey and Syria at the present stage. The conclusion is substantiates that there is a high likelihood of continued confrontation between Turkey and Syria in the short-term perspective. It is noted that the situation may change under the condition of the change of power in both countries, and coming to power of the government oriented towards mutually beneficial regional cooperation.