One of the more interesting rituals that functioned in Old Rus’ for centuries is the custom of cross kissing (крестноe целованиe), accompanying legal processes, such as taking oaths, public obligations, writing legal deeds, or concluding peace treaties. The earliest records of this ritual are evidenced clearly by the earliest chronicles and references in documents from that era. Due to the chronological structure and character of this work, which is clearly defined in the title of the article, the author’s attention is focused on the initial period of its functioning, until the end of the 13th century, in relation to contacts between Old Rus’ (Ruthenia) and Livonia. From Livonia, the parties participating in this ritual were Catholic bishops, Teutonic Knights, councillors from Livonian towns (Riga, Viljandi, Tartu and others), and even ordinary merchants. From Old Rus’, they were also participants in governments, merchants and warriors. From the historical sources, it can be stated here that the ceremony of kissing the cross was used quite commonly in legal acts between Old Rus’ and Livonia.