Icon painting has been one of the most important aspects of the cultural heritage of Romanian Armenians, contrasting with historical Armenia, where icon paintings were not widespread. Among more than ten iconographic forms of St. Gregory popular in Armenian art of the 18th century, only three are found in the icons created in Romania. The most common of these three forms created in Romanian-Armenian art, similar to Armenia itself and the Armenian colonies of the Diaspora, depicts the baptism scene of the Armenian royal family. Comparable icon paintings in the Romanian environment depict King Tiridates III of Armenia, Queen Ashkhen, and Princess Khosrovidukht kneeling before the Illuminator. In contrast to Armenia, the tortures of Gregory the Illuminator were often depicted in European art. In the 18th–19th centuries, a group of icons was also created in the Romanian-Armenian church environment, illustrating St. Gregory’s tortures and the martyrdom of St. Hripsime. Romanian-Armenian art portrays several biblical and pan-Christian worshipful saints as intercessors before the Mother of God, including St. Gregory. Alongside other saints of the General Church, St. Gregory served as the intercessor of the Armenian people. The Romanian-Armenian icons of Moldova exhibit a diverse range of styles, reflecting the various influences from Eastern European Orthodox and Catholic art during the 17th to 19th centuries. This article delves into the distinctive features of each iconographic type, comparing their versions within the same theme to unveil commonalities and differences. Details of the icons dedicated to St. Gregory’s life are described and analyzed based on biographical narratives.