The Bryansk Peter and Paul Monastery is one of the oldest in the Bryansk region, founded in 1280. The original wooden structures have not survived, but the Church of the Introduction, founded by Oleg of Bryansk, son of Prince Roman Mikhailovich, a well-known ruler and patron of the Bryansk land, remains. The monastery developed gradually, and by the mid-18th century, it owned villages and significant land holdings. However, in 1764, by decree of Catherine II, the monastery was stripped of all its possessions and abolished.

In 1830, Emperor Nicholas I approved the transfer of the monastic staff to Yelets, but thanks to the efforts of the Bryansk community and the Semykin merchants, who donated funds for restoration, the monastery was revived in 1833 to accommodate nuns. In the early 20th century, the Mogilevtsy brothers installed plumbing, and the last building was a hospital, which served as a military hospital during World War I. By 1917, the monastery included two churches and numerous buildings and cells. The name of Oleg Romanovich was almost forgotten, but Grand Duke Konstantin Konstantinovich revived its veneration by donating an icon and funds to the monastery.

In 1900, the Bryansk City Duma established September 20 as the day of remembrance for Saint Prince Oleg, and solemn services were held on this day. In 1903, the "Faithful Calendar of All Russian Saints" was published, which first mentioned the day of remembrance for Oleg of Bryansk. In 1918, the monastery was closed, and its premises were occupied by workers from the Bryansk Arsenal. In 1922, valuables were sent from the monastery to aid the starving in the Volga region.

With the onset of persecutions against the Church, the relics of the saint were in danger, and Archbishop Daniel (Troitsky) hid them under the altar of the Church of the Introduction. The secret was revealed only in 1995 when the relics were rediscovered.

The Church of the Introduction was built between 1702 and 1705 with funds from the Satov merchants. In 1826, the roofs were replaced, and in 1832, a portico was added. In 1923, the cathedral was closed, and later its building was used as an archive and cinema. In 1944, services resumed, and between 1986 and 1990, the church was restored. The monastery was renewed on October 7, 2002.