The Peter and Paul Monastery in Mtsensk was founded on the site of the former Small Ostrog of the Mtsensk Fortress. It is considered one of the oldest monasteries in the Oryol region and, according to legend, was established in the 12th century. However, it is more likely that its foundation dates back to the early 16th century, when Mtsensk became part of the Moscow state in 1500. Initially, the monastery was called the Peter Monastery.

In 1694, the Peter Monastery was relocated to a new site downstream of the Zusha River and was renamed the Peter and Paul Monastery. The construction of the monastery at the new location, on lands donated by the Protasov nobles (the current area of the railway station), began in 1695. The abbot Herman laid the brick Pokrovsky Cathedral with an altar dedicated to the holy apostles Peter and Paul, the construction of which continued into the early 18th century. Thanks to the efforts of benefactors and monks, by the mid-18th century, the monastery was fully rebuilt and improved. According to a description from 1764, there were two churches on its territory: the cathedral Pokrovskaya and the wooden Meeting of the Lord, as well as the abbot's and brother's cells, a bakery, a storage room, and a cellar. The monastery was surrounded by a brick fence about 350 meters long with towers and gates, built through the efforts of abbess Anfisa and abbot Feodul. Outside the fence were a garden, vegetable plots, and a farmyard. The monastery owned the village of Igumnova Slobodka with 74 peasants.

Two schools operated at the monastery, educating 151 boys. This was one of the first educational institutions in the Oryol region. Although there was no official almshouse, the monastery supported two disabled soldiers who had participated in wars with Turkey and Prussia. In 1764, the land holdings of the monastery were confiscated, and it was removed from the state list. In 1819, after the episcopal see was transferred from Sevsk to Oryol, the monastery was reinstated to the state list, and its superiors were granted the rank of archimandrites.

In the late 18th and the first half of the 19th century, active construction took place at the monastery, changing its appearance. The brick Znamenskaya Church (1813-1821) and a huge bell tower (1807) were built, almost all the buildings of the monastery were renovated or rebuilt, and the fence was reconstructed. The Pokrovsky Cathedral was painted, the iconostases were updated, and in 1809, a porch with a sacristy and library was arranged in place of the old bell tower. A cemetery formed next to the cathedral, where benefactors of the monastery and respected citizens were buried. Notable burials included the Protasovs, Khovanskys, Menshikovs, Yusupovs, and many monks and abbots. In 1891, General N. A. Belov was buried here. In 1839 and 1846, the monk Melchizedek lived at the monastery, whose ascetic activities led to a proposal for his canonization in 1918, but it was not realized due to difficult times for the Russian Orthodox Church.

The main relics of the monastery were considered to be four miraculous icons: Christ the Savior, the Tolga Mother of God, the Sign of the Kursk Mother of God, and the Tikhvin Mother of God. The monastery's library housed a 15th-century manuscript Gospel, a 1638 Trebnik, and a 1694 Gospel.

The monastery was closed in 1923. In the 1930s, it was used as a prison for dispossessed peasants and has survived to this day in a heavily ruined state. The Znamenskaya Church (without its top), the cell building, and remnants of the fence have survived. Only the altar apses of the ancient Pokrovsky Cathedral remain.