The Kiev-Pechersk Gymnasium, also known as the 5th Gymnasium of Kiev, was founded in Kiev in 1884 as a state male gymnasium.

The idea of creating the fifth male gymnasium was first discussed in the Kiev City Duma in 1882. At that time, the city mayor G. I. Eismann proposed to the curator of the Kiev educational district S. P. Golubtsov to open a preparatory gymnasium in the areas of Novoe Stroenie or Pechersk, which were far from educational institutions in the city center. Philanthropist Nikolai Artemyevich Tereshchenko offered to donate 100,000 rubles on the condition that a full-fledged eight-grade gymnasium would be opened with these funds. Local residents and Tereshchenko himself chose Pechersk for the location of the gymnasium, and he suggested naming it Kiev-Pechersk.

On February 21, 1884, a high decree was issued to establish the gymnasium. In the 1885/86 academic year, the preparatory, 1st, and 2nd grades opened. Initially, classes were held in a rented 11-room house of Zakhar Rybin on Nikolskaya Street, and in 1886 the gymnasium moved to its own building at the corner of Nikolskaya and Suvorovskaya, designed by engineer-colonel N. I. Chekmarev in the Russian style. In 1889, M. F. Mering became the honorary curator of the gymnasium, and in 1892 the first graduation took place.

The first director of the gymnasium, V. I. Petr, actively organized student excursions. Initially, these were one-day trips along the Dnieper, and in 1892 the graduating class went on a three-week trip to Crimea. Since then, Petr organized summer educational excursions for graduates to various places in the Russian Empire every year: in 1894 to the Caucasus, in 1895 to Finland, in 1896 to the All-Russian Exhibition in Nizhny Novgorod and further along the Volga, in 1897 to the Urals, in 1898 to the Caucasus and Crimea. In 1900, a large journey took place with 97 students to the World Exhibition in Paris, visiting Berlin, Dresden, Cologne, Switzerland, Prague, Vienna, Budapest, and other cities. In 1901, gymnasium students visited St. Petersburg, Finland, Sweden, Denmark, and Germany, and in 1902 they visited Crimea and the Caucasus again. Details of these travels were described in brochures mainly compiled by the students.

On May 26, 1899, the gymnasium celebrated the centenary of the birth of Alexander Sergeyevich Pushkin by unveiling a monument in front of the building at the initiative of teachers and students. The celebration program consisted of two parts: at the monument and in the gymnasium's assembly hall.

In the 1916-1917 academic year, the gymnasium had 8 main and one preparatory class, with 386 students enrolled, and the tuition fee was 60 rubles per year.

Since 1944, the building of the gymnasium became part of the Kiev Automobile-Road Institute and was extensively rebuilt for its needs.