Ukrainian agriculture belongs to the world Top-10 exporters of cereals and oilseeds. The option of increasing their contributions to the global food security by means of extensive expanding sown area in Ukraine has been already exhausted. To meet the contemporary challenges it is necessary to arrange intensive productions of wheat, barley, maize, sunflower, and soybeans with high yields. To monitor the regional dynamics over growing cereal and oilseed crops this research offers the aggregate rank assessments. They incorporate regional yields, shares of arable lands under wheat, barley, maize, sunflower, and soybeans, as well as shares of their productions by agricultural enterprises. To explore the existing disproportions between the used agricultural lands and obtained harvests this study recommends applying Lorenz curves and a set of inequality indicators such as Hoover and Theil indices, Gini coefficient, and also Ratio 20:20. Short-term and long-term prospects in enhancing Ukrainian contributions to the cereal and oilseed segments of the global food security were evaluated according to results of their leading exporters. To reach the levels of the chosen target countries, this research substantiates implementing optimal fertilizers application, rational land use, balanced pricing, developed transport infrastructure, as well as improved innovative, technological and market components in Ukrainian economy.