The first mentions of the Entry Church date back to 1552. In the "Monuments of Church Antiquities," Archimandrite Makary reports that two versts from the village of Dubenskoe, near a lake, Tsar Ivan IV the Terrible established a marble monument in the shape of a pillar, two arshins high and four vershoks wide, in memory of his campaign, and next to it, an icon of the Entry into the Temple of the Most Holy Theotokos. Later, the icon and the monument were moved to a wooden church in Dubenskoe, built shortly after the campaign against Kazan. In the mid-19th century, the icon of the Entry into the Temple of the Mother of God, adorned with a silver-gilded robe with pearls and stones, was located in the iconostasis of the stone Entry Church. There was also a marble pillar used as a candlestick in front of the carved image of the Savior in the dungeon. A copper silver-plated bowl for candles was attached to the upper part of the pillar.

In 1787, a cold three-altar stone church of the Entry into the Temple of the Most Holy Theotokos was built on the site of the ancient wooden church in the village of Dubenskoe. The right chapel was consecrated in honor of the Uncreated Image of the Savior, and the left, in honor of the Kazan Mother of God. A little earlier, in 1774, another warm stone church was erected in the village in honor of the Icon of the Mother of God "Consolation of the Sorrowful." In 1888, the parish had 426 Orthodox men and 478 women, and in 1904, 466 men and 500 women. The village had a church-parish school, where in 1888, 14 boys and three girls were educated.

The Church of the Entry into the Temple of the Most Holy Theotokos functioned until 1936, three years longer than the temple complex in the village of Vorontsovo. After the church was closed, a second floor and a coal boiler room were added to the building, and from 1955 to 1980, the former church housed a school. In the early 1990s, the building was used as a dormitory for workers, which significantly affected its condition: the walls were scribbled and painted over, and on the second floor, in the former teachers' room, the workers set up a toilet.

Around 2004-2005, reconstruction of the building began to convert it into an apartment building: new ceilings were erected, the walls were plastered, and utility connections were started. During the work, frescoes were discovered under the old school plaster, which are now lost. Church utensils, such as censers and chains, were also found. Notably, when laying sewage and water supply, the ground in the altar area was excavated, and the remains of several people were discovered, one of the skulls having a round hole. The remains were left unburied for some time and were then buried.