This study identified the icon of Virgin Moscovita and the icon of the Holy Mandylion, described in Konstantinos Dapontes’ writings, with the icon of the Virgin and the icon of the Holy Mandylion preserved in his family monastery Evangelistria in Skopelos island. We can now retrace the “biography”of these two artefacts, the history of their creation, donation, and multiple “transfers” of the two icons. This study is an important contribution to the history of the early modern period in the Balkans. The icon of the Virgin Moscovite was donated to Konstantinos Dapontes by his benefactor Konstantinos Mavrocordatos in 1741 in Iasi, and the the icon of the Holy Mandylion was donated to Dapontes by his “maître spirituel”, the patriarch of Antioch Sylvester in 1762.