This paper examines the particularity of the philosophy of history of the German thinker Oswald Spengler. Through the analysis of his two-volume masterpiece The Decline of the West and a shorter work Man and Technics his cyclical understanding of history along with the peculiarities of cultures as the main protagonists of history are outlined. Spengler deems of cultures as organisms and therefore closely examines their life cycle with a special reference to the phase of civilisation. The focus is specifically put on the destiny of Western Europe as the analysis of its decline and the foreseeing of its future are seen as the main topics of his work. The critique of his era is neither left aside accompanied by a thorough analysis of the dehumanisation of the human being caused by the abuse of technics. In order to get a different perspective of Spengler's philosophy of history this paper also studies closely the work of Samuel P. Huntington, an American political scientist, which is thought to bear some resemblance to Spengler's theory and therefore possibly inherits it. For the same purpose the opposed view of history of the Russian philosopher Nikolai A. Berdyaev, Spengler's contemporary, is also presented. In the final chapter possible oversights and shortcomings are analysed in order to give a final judgement on the value of Spengler's philosophy of history.