Saints Cosmas and Damian are considered the patrons of blacksmiths, which is why until 1794, the Church of Cosmodemyansk was located on Bogoyavlenskaya Street, near the forges. Later, both the forges and the church were moved to the Moscow Gates.

The church suffered from a fire in 1754, and the bell tower was only built in 1836. In 1881, the main iconostasis was renovated and gilded, and in 1886, the side altars' iconostases were installed, decorated with carvings and gold. In 1888, the church was painted, and the existing artwork was restored.

In the inventories of 1626 and 1685, it is mentioned as the Church of St. Nicholas the Wonderworker behind the shops, wooden, with a tent roof, in the old fortress, with an altar dedicated to Cosmas and Damian. In the 18th century, the church was located near the current Bogoyavlensky Church. In 1754, the wooden church burned down, and in 1755, a new stone church was built in honor of St. Nicholas. In 1794, according to a new plan for Kaluga, the Nicholas Church was dismantled and moved to a new location, with construction completed in the 18th century.

The main altar of the new church was consecrated in the name of the Uncreated Savior, but the people continued to call the church Kozmodemyansk, although only one of the side altars was dedicated to these saints, while the other was in honor of St. Nicholas.

Before the revolution, the church housed valuable items, such as a Gospel on blue paper (1755) and a prayer book from 1658. The church was famous for the icon of the Mother of God "Suffering," adorned with a silver robe, pearls, and precious stones. It also housed the Pochaev Icon of the Mother of God, brought from the Pochaev Lavra, which was lowered for veneration once a week.

Despite its unique beauty, the church suffered from Soviet vandalism. Priests Antoniy (Kobelyov) and Nikolay Vylezhinskiy were arrested in 1926 for "anti-Soviet agitation." Antoniy was exiled to the Belgorod region and shot in 1931, while Nikolay's fate after his exile to the Nizhny Novgorod region is unknown.

In 1937, the church was closed and used as a temporary detention center. The closure was accompanied by desecrations and sacrilege. Komsomol members attempted to paint over the frescoes, but the images of the saints showed through the paint. During an attempt to scrape off the images, one of the Komsomol members fell dead. When removing the bells, one participant fell and was crushed by a bell.

After its closure, the church was used as an isolation facility, then as a garage and warehouses. In 1960, it was recognized as an architectural monument. Despite this, the church continued to deteriorate, and its valuables disappeared.

On July 17, 1992, the church was returned to the Kaluga Diocese and became an Archierial Courtyard. On August 27, 1998, Archbishop Kliment consecrated the altar of the central altar, and services resumed in the church.

From 1992 to 1996, the rector was Archpriest Nikolay Sukhodolov, and from 1997 to 2016, Archpriest Georgiy Gafarov. Since May 23, 2016, Archpriest Sergey Tretyakov, Vice-Rector of the Kaluga Theological Seminary, has been appointed as the rector.

Services and restoration work continue in the church. A monument to those fallen in Afghanistan, Chechnya, and other "hot spots" has been erected in front of the southern facade, making the church also a memorial for soldiers.

Two Sunday schools for children and adults operate at the church. Spiritual and educational discussions are held on Saturdays, and pilgrimage trips are organized.