The paper is a complex study of the history of the involvement of Woodrow Wilson (the 28th President of the USA, 1913-1921), in the fate of Armenian people after WWI and the Republic Armenia (1918-1920), especially in determining the boundary between Armenia and Turkey. It presents an analysis of Wilson's Arbitral Award according to the international law and the United Nation's official methodology. The article focuses on the historical background, legal aspects and political implications of Wilson's Arbitral Award (November 22, 1920), officially titled: Decision of the President of the United States of America respecting the Frontier between Turkey and Armenia, Access for Armenia to the Sea, and the Demilitarization of Turkish Territory adjacent to the Armenian Frontier. The Arbitration's significance goes beyond Armenian-Turkish and Armenian-US relations. Border conflicts are still relevant issues on the regional and international agenda. American involvement in the Middle East is one of the key components of the United States' present foreign policy. An accurate and a broad understanding of the nuances of the extremely complex legal situation in the region and the bases for the behaviour of the players can be vital for the security, political and economic interests of the region. Moreover, due to the active participation of the United States in the Armenian-Turkish relations through Wilson's Arbitration, the Arbitral Award becomes a logical starting point for a stronger historical, political, and legal understanding of the conflict-prone region. The article also contributes to the better understanding of President Wilson's policy towards the Middle East during the dramatic period of 1917-1921 and its possible consequences for critical relationships in the region today.