The article tends to show the hidden semantics of Old Ukrainian customary law procedures concerning the land boundaries’ marking. The author used a comparativehistorical approach. At first, the main significant elements of boundaries marking and making were distinguished in the range of historical sources (the Book of Kyiv Chamberlaine Court, City Book of Poltava, Kyivan Rus princes’ charts from 14 c., «Rus’ka Pravda», and South Russian acts from 17 c., which are ethnographically close to Ukrainian material). These elements comprise: circular movements («obyizd», «obkhid», «zayizd», «uyizd»), sings («gran’», «kopci»), and especially oaks and trees with bee-hives («bort’»). Since in the cognate Indo-European traditions, an oak is known to be a tree of a thunder-god, a comparative analysis of land boundaries setting laws of Hittite, Old Indic, and Old Irish traditions was undertaken. Mythological notion of an oak and bees in Baltic other Indo-European folklores were considered as well. All elements of Old Ukrainian rite of boundary setting have ancient mythological semantics. The circular motion around a certain territory had special semantics in the Hittite and Old Indian traditions, where the ruler undertook a yearly tour of his domain. In Ancient Irish laws, an oak was one of the main boundary marks. An oak as a tree that belonged to the thunder-god had a specific semantics in Baltic beliefs, where it was connected both with bees and Perkons. The approach suggested in the article is a new, original one, and may enhance reconsidering the significance of old chancery documents as a possible source for studies in mythological outlook survivals among the inhabitants of old Ukrainian territories, as well as to trace the inheritance of law procedures at stylistic level from the time of Kyivan Rus up to 17 c.