The article is devoted to the study of the activities of students of the oldest educational institution in Western Siberia – the Tobolsk male gymnasium during the revolutionary upheavals of 1905-1907. Attention is paid to the analysis of the features of the educational process, reflected in the protocols of pedagogical councils and reports of the director of the gymnasium P.I. Panov. It is noted that despite the control over the behavior of the students of the gymnasium by the director, teachers, class mentors and parents, the students were gradually drawn into political processes covering the whole country. The penetration of one revolutionary proclamation into the walls of the gymnasium after the events of January 9, 1905 led to a long conflict between the students of the educational institution. There was a strike of a number of students, which resulted in a refusal to attend classes due to the failure of the gymnasium administration to fulfill the requirements of the gymnasium students. The authors consider the main demands put forward by the pupils of the male gymnasium in the autumn of 1905, which were presented to the leadership of the educational institution in the form of a petition containing 29 points. It should be taken into account that the petition was sent from European Russia to unite the demands of secondary school students to change the educational process. The paper concludes that the high school students opposed prohibitions and restrictions, did not have a clear political program and action plan, so the protests were spontaneous and chaotic. In this article, the authors use a representative source base of unpublished materials from the funds of the State Archives of Tobolsk and Tomsk, related to the history of the Tobolsk male gymnasium.