This paper explores the South-South migration of high-skilled migrants with special focus on waves of Indian diaspora to Southeast Asia mapped within dynamic routes of Asia Pacific region. We trace the historical and socio-economic implications of this migration, particularly in host countries such as Singapore and Malaysia vis-à-vis India. Due to the nature and dominance of highly skilled Indian migrants in the sector of Information and Communication Technology, the paper will largely reflect the implication of this sectoral boom. The paper is structured into four sections. In the first section, we contextualize the migration of Indian skilled workers to Southeast Asia followed by a historical account of the migratory relations between Indian and the Southeast Asian countries. The third section will briefly focus on the destination countries of Singapore and Malaysia in terms of the dimensions mentioned above. The final section will serve as a summary of the paper and will highlight the observable trends of highly skilled Indian migration to Southeast Asia. This paper is an attempt to induce academic curiosity to the understudied route of South-South Migration which holds much relevance in the current geopolitics of Asia.