Bulgaria and Romania are characterized by a higher percentage incidence of rural population than other European nations and a significant diffusion of less favoured areas with limited agricultural surfaces as well. The objective of this paper was to investigate, via a quantitative approach, effects and relationships among funds allocated by the second pillar of the Common Agricultural Policy on cropping specialization. Furthermore, subsidies and other financial supports assigned by specific agricultural and rural policies have had a positive role in areas at risk of marginalization and characterized by out migration issues. In the quantitative analysis we used the data published by the European Union in the Farm Accountancy Data Network (FADN) since 2007 to 2012. In Bulgaria, as a consequence of a greater diffusion of large size farms, the financial subsides allocated by the EU, throughout Single Area Payment Scheme and towards crops have been significant in Romania and Bulgaria. Romania has pointed out a positive impact of financial aids paid to less favoured areas in order to reduce the rural marginalization and countryside depopulation.