ASEAN countries have made a considerable progress in terms of the economic development and competitiveness increase since Asian crisis of 1997–1998. Furthermore, in order to reinforce all the positive achievements and to enhance the growth potential the ASEAN Economic Community was established in 2007. Thus, the competitiveness has been officially set up as an integral part of the development strategy for the whole Southeast Asian region. Currently, the interrelation between economic development, competitiveness and progress within the ASEAN Economic Community has been recognized as essential by the researchers worldwide as well as by the policy-makers of ASEAN member countries. It has already become an inherent factor of economic policy. Because of the shortage of up-to-date statistical information the assessment of ASEAN competitiveness has been complicated. The Global Competitiveness Index (GCI), a comprehensive tool developed by the World Economic Forum, remains the core reference in the analysis of all competitiveness-related subjects. At the same time, there is a more regional-specific Index elaborated by the Asia Competitiveness Institute. This local think tank utilizes a more nuanced and holistic approach to the assessment ASEAN member countries’ competitiveness. The author presents an overview of the current status of ASEAN competitiveness’ analysis and assessments. The advantages and limitations of the approaches used in the Global Competitiveness Index (WEF) and the ASEAN Competitiveness Index (Asia Competitiveness Institute) as well as the resulting implications for the policy-making are scrutinized. It is concluded that the benchmarks for the comprehensive competitiveness assessments have been shifted from global to regional and from short-term to long-term to reveal specific issues for ASEAN. The key achievements and omissions of each ASEAN country are considered through the impact of Asian crisis of 1997–1998 and Global crisis of 2008–2009.