The Church of the Entry of the Most Holy Theotokos, also known as the Peter and Paul Church, is located on the high rocky left bank of the Zusha River, on the territory of the former Small Ostrog of the Mtsensk Fortress. In the 16th and 17th centuries, it served as the cathedral church of the male Peter Monastery, which was considered one of the oldest in the Oryol region. According to tradition, the monastery was founded in the 12th century, but it is more likely that this occurred in the early 16th century when Mtsensk became part of the Moscow state in 1500.

According to the 1625 census book of the city of Mtsensk, there were two wooden churches in the Peter Monastery: Peter and Paul and the Entry of the Most Holy Theotokos with a chapel of the Prophet Elijah, renovated with the funds of the first tsar from the Romanov dynasty, Mikhail Fyodorovich. Next to the churches were the cells where the abbot and monks lived. In the 1670s, the nobleman S. V. Ragozin built a stone seven-domed cathedral church of the Entry of the Most Holy Theotokos in the monastery with three altars: the Entry of the Theotokos, Saints Peter and Paul, and the Holy Prophet Elijah. It is likely that at this time the second wooden monastery church was dismantled. In 1694, the Peter Monastery was moved to a new location downstream of the Zusha and became known as the Peter and Paul Monastery, while the Entry Church was transformed into a parish church. The bell tower of the church was built at the turn of the 18th and 19th centuries. Before World War I, it was planned to establish a skete at the Entry Church, affiliated with the Peter and Paul Monastery, but this was not realized.

The church was closed in the 1930s, and during the occupation of Mtsensk, the Germans used it as a stable. It was reopened after the Great Patriotic War in 1947. Four white stone gravestones from the first half of the 16th and mid-17th centuries, discovered by art historian T. A. Timasheva, have been preserved in the churchyard. One of the stones contains the inscription: "In the year 7164 (1656), on the 18th day of January, the servant of God Ivan Stefanovich Ragozin passed away in the monastic order as a schemamonk Iev."