The purpose of the study is to analyze the living and learning conditions of students of gymnasiums in Ukraine in the nineteenth and early twentieth centuries, which were formed under the influence of the educational policy of the then tsarist government. The research methodology involves a combination of general scientific (analysis, synthesis, generalization, comparison, systematization), special historical methods with scientific principles of objectivity, systematicness, historicism. The scientific novelty of the article lies in the fact that for the first time the problem of gymnasium education in Ukraine of the nineteenth and early twentieth centuries is analyzed. in the context of the history of one of the oldest educational institutions. A significant number of archival sources have been worked out, some of which have been introduced into scientific circulation for the first time, forms of financial assistance to students of gymnasiums have been highlighted, and attention has been focused on the possible use of historical experience in modern conditions. Conclusions. In the second half of the nineteenth and early twentieth centuries. in Russian-controlled Ukraine, a certain system of care, control and support for gymnasium students was formed. The management of educational institutions provided supervision over the living and learning conditions of high school students, encouraging the parents of students or the owners of the apartments in which they lived to create favorable conditions for the preparation of classes, to control their implementation, to be the most good example for students. Therefore, the issue of choosing an apartment, a house where a high school student should live, was approached very responsibly, giving permission to owners with an impeccable reputation in society. Taking into account that some of the students of the gymnasiums studied at their own expense, were from poor families, a system of material support was created through the provision of scholarships, reduction of tuition costs or even exemption from payment for the children of teachers who worked for at least 10 years in lower and secondary educational institutions of the Ministry of Public Education. Of course, one should not overestimate the effectiveness of the then system of gymnasium education. There were cases of expulsion of students from an educational institution due to failure or non-payment of tuition fees, examples of antisocial behavior of individual high school students were recorded. All this indicates that it was not always possible to cover all students of gymnasium institutions with attention, control and support, but certain elements of the former system can be used at present. In particular, this concerns closer ties with parents or guardians of children, expanding the practice of awarding incentive scholarships both from the state and from individuals.