In summer 1650, on initiative of Poltava citizens, was founded a monastery in honor of erection of honest and healing cross of God. The monastery was established by sons of Mgarsko-Lubensky monastery of the Transfiguration and their head Father Superior Kalistrat as a memorial to first victories in battles with Poland.
Since that time this Monastery became the most southern one among city, or regiment, monasteries of Hetman state in XVII century. Money for the monastery building was given by Poltava squares and Cossacks officers Ivan Iskra, Ivan Kramar and colonel Martyn Pushkar. During Poltava period of the Great Northern war, the monastery was a post of Charles XII.
Poltava Monastery was important educational centre of Hetman state Southern part. At the origin of it there was Eugene Bulgaris — Slavic and Kherson archbishop; he was a good friend of French educator Voltaire, former librarian of Katherine II. Due to his efforts the Monastery had the largest library at the region. There were even some editions of XVI — XVII centuries. Under the patronage of the monastery there was a school of singers; later it was transformed into Slavic seminary.
The real pearl of the whole Monastery complex is Khrestovozdvizhensky cathedral (built between XVII-XVIII). Money for the cathedral building was given by few Poltava colonels and two hetmans — I. Samoylovich and I. Mazepa.
Near the cathedral there is a first high-rise of Poltava — the Monastery bell tower (1786); it high is 154,20 ft. Its project author is archbishop Nikiforos Theotokis. At the other side of the cathedral there was Saint Trinity church (1750). During the Second World War the church was ruined. Later it was built again, in 1999; the project was made by J. Oleynik. In the Saint Trinity church were buried such people as archbishop John (O. Petin), bishop Tychon (P. Klytin), archibishop Parpheny (P. Levitsky), Poltava and Kremenchug metropolitan Pheodosy Dykun-Vakoluk. At the end of XIX century there was erected St. Simeon church at the territory of the Monastery.