The Nikolskiy Greek Monastery, also known as Nikola Stary near Bolshoy Krestets or Nikola Bolshaya Golova, is one of the oldest monastic establishments in Kitai-Gorod, founded in 1390. Saint Nicholas was one of the most revered saints in Russia, and in Kitai-Gorod by 1917, 13 out of 56 altars were dedicated to him. The icon of Saint Nicholas of Mozhaisk adorned the Nikolskiye Gates of the Kremlin.

Historical records link the monastery to the Greeks, and it possibly served as a refuge for them in Moscow. The monastery was also used as a place of confinement for errant priests.

In the mid-16th century, Ivan the Terrible transferred a plot of land between the Zaikonospassky Monastery and the Printing House to Athos monks for temporary residence. The Greeks built the Church of Nicholas the Wonderworker, but the monastery remained subordinate to the Moscow Patriarch.

In 1648, Archimandrite Pachomius of the Iver Monastery brought a copy of the Iver Icon of the Mother of God from Athos. Before the construction of a special chapel at the Resurrection Gates, the icon was housed in the Nikolskiy Monastery. For this, Tsar Alexei Mikhailovich transferred the monastery to Greek Archimandrite Dionysius, allowing services to be conducted in Greek. A year later, only Greek monks remained in the monastery, and it became known as the Nikolskiy Greek.

In the 1720s, the old cathedral was replaced with a new stone one thanks to the efforts of Moldavian prince Dimitrie Cantemir, who had a court between the monastery and the printing house. The monastery became the family burial place of the Cantemirs. Between 1734 and 1736, the heirs of Cantemir built an upper church over the cathedral in honor of the Iver Icon, later renamed to the Dormition. In 1767, Matvei Cantemir renovated the church in honor of Saints Constantine and Helena.

After the fire of 1737, the monastery was restored and remained largely unchanged until the end of the 19th century. M. Kazakov updated the main cathedral, which by that time had become quite dilapidated. It acquired a classical appearance with porticos, a large dome, and a turret, known from old photographs.

A major reconstruction of the monastery began in the late 19th century. In 1893, new buildings for cells and income premises were constructed along the borders of the monastery according to the design of G. Kaiser and K. Busse. In 1902, G. Kaiser erected a building in the Russian style with baroque elements on Nikolskaya Street. It was entirely commercial, with a chapel of Saint Nicholas the Wonderworker and a bell tower in the center.

In the early 1920s, the monastery was closed, and in 1935, the main cathedral was destroyed. Before the demolition, the Romanians purchased the remains of Dimitrie Cantemir. The remains of Antioh Dmitrievich were not taken, as he was considered a traitor, and his grave disappeared during the demolition of the monastery, along with the graves of other notable figures. Some tombstones were transferred to the museum at the Donskoy Monastery.