The Association of Southeast Asian Nations (ASEAN) is one of the most important regional political and economic organizations in the world. It demonstrates tremendous vitality and plays a critical role in international economic systems. Since the end of the Cold War, especially with the continuous advancement of regional economic integration in Southeast Asia, the trade and economic relations between the ASEAN (including Brunei, Cambodia, Indonesia, Laos, Malaysia, Myanmar, the Philippines, Singapore, Thailand, and Vietnam) and global major extraterritorial powers, i.e., China, America, Japan, India, and South Korea (hereinafter referred to as CAJIK), have become increasingly strengthened and complex. With the yearly bilateral trade data of CAJIK and the ASEAN countries during 1992-2015, we analyzed the trade patterns and trade interdependence between CAJIK and the ASEAN since 1992. The results showed that: (1) Total trade volume increased by 5.6 times between the ASEAN countries and CAJIK. Specifically, the total trade between China and the ASEAN achieved the greatest development and increased by up to 50.6 times. However, the total trade volumes between America, Japan, and South Korea and the ASEAN grew slowly. (2) Of the ASEAN countries, Singapore, Malaysia, and Thailand were the traditional largest trading partners with CAJIK. However, Vietnam has become a new growth pole in ASEAN trade in the 21st century, which is predicted to be the largest trade country in Southeast Asia. (3) The trade between CAJIK and the countries of Mainland Southeast Asia (MSEA) increased much faster than those of Insular Southeast Asia (ISEA, including Indonesia, Malaysia, the Philippines and Singapore), about 11.2 times versus 4.1 times respectively, which highlights the greater potential of foreign economic and trade cooperation in MSEA. This study contributes to understanding the general evolution characteristics of trade between the ASEAN and extraterritorial countries, and provides inspiration for conducting research on geoeconomic cooperation and its effects between countries, especially in border areas.