The 14th and 15th centuries are considered the “darkest” period in the archaeology of medieval Rus’. The watershed of the Desna and Oka river basins, located at the borders of the modern Bryansk and Oryol regions, is one of the least studied areas in terms of political history. During these centuries, it was situated at the frontier of the principalities of Bryansk, Karachev and Novosil’ (the southernmost on the Upper Oka), which were “squeezed” between the Grand Duchies of Moscow, Lithuania, Ryazan’, and the Golden Horde. New archaeological and numismatic findings made by the expedition of Bryansk State University provide material evidence of the military-political events of the last third of the 14th century. Additionally, the correlation of these findings with specific events allows for more precise dating of various types of religious artifacts, military equipment, and monetary and weight items. Key dating finds (apart from ceramics) at the Navlya settlement include a rowel spur of type VIII (according to O. Dvurechenskiy, 2014) and a copper alloy encolpion depicting the Archangel Sachiel and Saint Sisinnius. This encolpion is a double recast from the original. The spur belongs to a type characteristic of the transition period from chain mail to plate armor, a time when combined armor prevailed in Europe. Based on analogs from Poland, Czechia and Galicia, the Navlya specimen can be dated from the second half of the 14th century to the early 15th century. The encolpion can be dated to approximately the same time. In this border region, many military events occurred in the late 14th and early 15th centuries, which could have resulted in the deposition of valuable and intact items in the cultural layer. These events are also associated with other finds of rowel spurs, but more frequently of later types, as well as similar encolpia and icons throughout the Southeast of Rus’, including the Seim and Psel regions. However, for the Navlya finds, the chronology can be narrowed to the end of the 14th century, thanks to the discovery of a hoard of Jochid dirhams (dang coins), as well as hoards and individual coins of Severskaya minting at the Navlya.