Among problems that arise during study of Gregory Skovoroda’s life and works, there is problem of sources, which is one of a primordial importance. It is fact well known enough that in his works and letters Gregory Skovoroda mentioned very few authors who had been sources of inspiration to him. Therefore, one of the main tasks for those who study life and works of the Ukrainian philosopher is to discover his sources, analyzing his connections to those authors that he mentioned throughout his works and the correspondence. One of these episodic mentions in Skovoroda’s letters is the mention of Boethius — poet, writer, politician, philosopher, and theologian of the Early Middle Ages. The comparative study of both the text of Boethius’s “De concolatione” and Gregory Skovoroda’s works reveals a startling similarity of these images and symbols, concepts and ideas, conceptual, me thodological and compositional approaches. Sometimes there are even almost textual allusions, which make an impression of though not literal and completely precise but almost quotations or a loose translation of that had sometimes been memorized before, learnt by heart. Thus it is to admit that Gregory Skovoroda made a good acquaintance with the Boethius’s ‘golden volume’ yet during doing his studies in the Kiev Mohyla Academy, having cherished the love for this book throughout his life.