The article examines the theoretical concept of interregionalism in the context of the evolving framework between the European Union (EU) and the Association of Southeast Asian Nations (ASEAN). As the EU’s first free trade agreement (FTA) with an ASEAN country, the EU-Singapore FTA is a pathfinder agreement that signifies a new phase of interregionalism and the EU’s new Asia strategy after the Treaty of Lisbon. The article argues that the innovative designs of the EU-Singapore FTA will shape the normative development of EU-ASEAN relations in the post-pandemic era. It also cautions that a comparative analysis of EU and US agreements reveals deficiencies in the FTA that require remedies. To buttress the contention, key provisions on ASEAN cumulative rules of origin, banking and legal services and non-tariff barriers are analysed in light of contemporary Asian agreements. The research further provides insight into the effectiveness of new-generation rules on geographical indications, competition, and investor-state arbitration and mediation. Hence, the findings contribute to the understanding of interregionalism and the EU’s Asia-Pacific trade and investment agreements from global and interdisciplinary perspectives.