The headwaters of fluvial systems on the East European Plain between the boundaries of the Marine Isotope Stage 2 (MIS 2) and MIS 6 glaciations evolved during the last 150,000 years. At least three main events of high surface runoff caused intensive erosion: at the end of MIS 6, at the end of MIS 2 and in the Middle Holocene. Erosion developed in the territory with variable resistance of geological substrate, from hard-to-erode tills to weak sandy deposits. All erosional features in moraines formed in the pre-Holocene time. Even relatively large forms, such as balkas (small dry valleys), have not yet reached concave longitudinal profiles. A general tendency of their development was deepening. Short episodes of incision occurring during climatic events with increased water flow alternated with long periods of stabilization. Sand-covered areas are most favorable for linear erosion. The gullies formed in the Middle Holocene developed concave longitudinal profiles. The diversity of catchment areas, initial slope inclinations and sediment properties causing their resistance to erosion led to greater differences in the relief features and evolution of the upper reaches of the fluvial systems within the MIS 6 glaciation area compared to the more uniform landscape conditions in the extraglacial regions.