The relationships between Greek and Romanian churches during the past centuries were multilateral and considerable, especially with Holy Mountain monasteries. However, the history of relations Orthodox sister churches is not yet fully known and valued. The protection and restoration of common cultural heritage monuments, least appreciated and badly restored, remains current. Irinupoleos Gregory (1764-1846) was confirmed in metropolitan famous Greek monastery of Vatopedi – Irinupoleos Gregory. Life and work of the leading figures in the first half of the nineteenth century, remains insufficiently investigated. The article comes to fill the gaps about the life and activity of Gregory Irinupoleos – remarkable personality from the history of Athos & Bessarabia at the end of the XVIII-th century – beginning of the XIX-th century. We attempt to elucidate, based on historical documents (found in the archive of the monastery Vatopedi and Moldovan National Archives) and to present an overview of the life and work of the Holy Mountain Metropolitan of Bessarabia (Chisinau).