The current study explores the role of alfalfa (Medicago sativa L.) as a valuable perennial legume crop that serves as an effective precursor in crop rotations for maize and winter wheat cultivated on grey forest soils in the Vinnytsia region of Ukraine. Alfalfa is recognized as one of the most productive and valuable forage crops, capable of addressing the deficit of plant-based protein in livestock feed across many regions. It is unmatched in terms of protein quality and essential amino acid content. However, key factors limiting its cultivation include the decline of the livestock sector, reliance on monotonous forage systems, and soil acidification, which reduces alfalfa’s productivity, nutritional value, and longevity in grass stands. The study analyzes the agrobiological properties of alfalfa in improving soil structure, increasing organic matter content, and stimulating microbial activity. The results highlight its impact on enhancing soil fertility, improving the productivity of subsequent crops, and reducing the need for mineral fertilizers. The highest productivity of alfalfa stands was recorded under the second management regime – cutting at the early flowering stage. It was found that the early-maturing semi-dwarf winter wheat variety Bilotserkivska outperformed the mid-early Tsarivna variety by 0.27–0.54 t/ha regardless of sowing time. Among maize hybrids, Bilozirskyi 295 SV showed superior silage yield compared to Monika 350 MV across all fertilization levels. The highest yield (28.9 t/ha) was recorded in Bilozirskyi 295 SV at the wax ripeness stage with nitrogen application at N₁₃₅. As a rotation crop, alfalfa facilitates the development of stable and highly productive agroecosystems, reduces the need for mineral fertilizers and agrochemicals, and thereby increases the efficiency and environmental sustainability of farming. Under the conditions of climate change and resource conservation needs, the integration of alfalfa into crop rotations is a crucial direction for the sustainable development of agricultural production.