The icons brought to Italy from the East during the first centuries of Christianity were especially revered among believers, and subsequently even their copies were often no less revered. After the capture of Constantinople by the crusaders in 1204, Greek icons began to appear in those areas of Italy where they had previously been a rarity, they were reproduced, these copies became images unto themselves, made to order, and, therefore, acquired their own semantic significance. The Byzantine icon of the Virgin, the Hodegetria, was skillfully created in the first half of the thirteenth century in Siena. After defeating the Florentines at the Battle of Montaperti, the Sienese declared the Mother of God their patroness in 1261. Soon, the copy of the Byzantine icon was made to be placed in the new altar of the city cathedral. Later, the work of a Sienese master became no less revered than the original Byzantine image and received the name of “Madonna del voto”. Its origin demonstrates that it was of paramount importance for the inhabitants of the city. Most likely, this was the first precedent of this kind. The very fact that a local artist painted an image that, on the one hand, embodies the Mother of God’s intercession for his hometown, and, on the other, clearly shows conscious, but not a complete adherence to the Byzantine prototype, significantly influenced the development of painting in the late thirteenth-century Siena. Relatively scarce attention has been paid to this event in the secondary literature. Such a research on the causal relationship between the specific circumstances of ordering a sacred image and its pictorial realization allows us to consider more widely both the issue of copying Greek images in Italy and the formation of the Sienese pictorial art in the second half of the thirteenth century.