The song traditions of the Oka River basin are among the least studied of Russian ethnic terri­tories. Meanwhile, they are particularly interesting to ethnomusicologists, as they most likely belong to archaic East Slavic cultures. Moreover, it has been documented that they have become the source of many Russian traditions of late formation. Based on wedding songs of the tradition localized in the left-bank territory of the upper reaches of the Oka (Kaluga-Oryol borderland), the Upper Oka-South Russian correspondences are studied in detail for the first time in this article. The author’s goal is to isolate those phenomena in the studied materia that are regularly found in the wedding fund of the South of Russia and are perceived by experts as relevant regional features. As a result of the research, the following were attributed to the latter: the structure of the ritual song cycle with the allocation of praise songs as an independent genre group, the fund of musical and rhythmic types and their varieties, as well as peculiar compositional versions of wedding songs that combine the studied area with the system of South Russian song traditions.