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One of the main objectives of the European Union since its foundation has been the harmonization of the levels of development of its member country. In order to achieve this, the European Commission adopts two types of policies, regional policies and pre-membership policies, with the aim of strengthening “European cohesion.” Measured by the level of economic convergence, this cohesion seems to be well established at country level but remains mixed at the regional level. The level of economic development, represented by the GDP per capita, is not only an indicator of poor regions’ eligibility for European cohesion funds; it is also a tool for the commission to evaluate these policies. Nevertheless, “harmonious development” cannot be reduced to a single economic dimension. In this article, we study the development of the countries and regions of the EU-27 according to two different conceptions of development—economic and human—based on two different indicators: i) the GDP per capita and ii) the HDI. The convergence analyses that were carried out highlight some relatively conflicting trends in the European Union over the last two decades.