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This paper is a critical historical analysis of the trajectory of geo-political and economic relations between India and Singapore. This paper argues that India’s perception of its interests and its geopolitical orientation towards the Cold War prevented India’s security and economic integration with Southeast Asia. Apart from geopolitics, the economic orientation of India was also a critical factor that influenced the trajectory of India – Singapore economic engagement. However, there was a dramatic change after the Cold War ended. The structural change from bi-polarity towards a unipolar moment transformed both geopolitics and economic engagement. Moreover, India’s own economic orientation had also changed by the end of the Cold War. In sum, this paper attempts to elucidate upon how ideas construct economic and political interests and how geopolitical interests, once constructed, drive economic relations. [ABSTRACT FROM PUBLISHER]