The article reveals the peculiarities of intercultural paradigmatic shifts in the philosophical and pedagogical thought of Ukraine in the second half of the 19th and early 20th centuries. It has been proven that Ukrainian philosophical and educational thought (despite the fact that it objectively bordered with the Russian one and actively fits into the pan-European philosophical and pedagogical algorithm) had a number of specific national concrete-cultural features and colours. Its image was closely related to the formation of the “soul of the Ukrainian people”, which was formed by a combination of mental, cultural and moral characteristics. The matrix of paradigmatic shifts in philosophical and pedagogical thought of this period was focused on the semantic, ontological dimensions of human spirituality, pedagogical factors of personality development, the formation of the national discourse of educational science as a certain theoretical integrity. It has been confirmed that the philosophical and pedagogical thought, which unfolded within the framework of socio-political development of scientific and educational institutions and which performed a human-creating function in culture, was characterized by a tendency to create an intercultural “philosophy of teaching and education”, which became the background for pedagogical constructions of our (that?) time. On this basis, the most important constants in the development of education of this period are determined, which have heuristic significance and are in many respects compliant with modern educational transformations, which require comprehensive understanding, primarily from the standpoint of pedagogical anthropology.