The Orlov Classical Gymnasium was established on the basis of the Main People's School. The stone two-story building, constructed in 1796 specifically for this school, turned out to be suitable for the gymnasium as well. However, after the transformation of the gymnasium in 1833 into a 4-class educational institution according to the 1828 Charter, the building became cramped for the increased number of students, including those from the noble boarding school that existed since 1835 on 2nd Kurskaya Street and was funded by the state and partially by the nobility of the province. In 1850, 153 people were studying at the gymnasium, of which 124 were children of nobles. After the opening of three lower parallel classes in 1861, the number of students increased to 244, including 196 nobles and 9 representatives of the clergy, while the rest were from taxable classes.

In 1861, the Karachev nobleman, Guards Rotmistr N.V. Kireevsky, donated funds for the expansion of the building. Education at the gymnasium in the 60s-70s of the 19th century lasted eight years. In the last three years, students studied in one of two departments, philological or natural-mathematical, but the subjects remained general education: Law of God, Russian, Latin and Greek languages, mathematics, natural science and physics, history, geography, German and French languages, drawing, drafting, and penmanship.

According to the charter of gymnasiums and progymnasiums from November 19, 1864, gymnasiums were divided into general and classical. The Orlov Gymnasium became classical on March 17, 1863, a seven-class institution with an eight-year course of study, where the seventh class was divided into two years. Graduates of classical gymnasiums could enter universities. In 1867, the Alexander Nevsky Church was built in the gymnasium building with funds from N.V. Kireevsky.

Today, in the gymnasium building located at Voskresensky Lane, 5, a federal architectural monument, is the Faculty of History of the Oryol State University.