This paper examines the challenges and development opportunities of ASEAN and selects the EU as a comparative candidate. Conclusions are drawn under the structure of integrating the four core components: development history and achievements, differentiated comparison, challenge profiling, and opportunity outlook. Even though ASEAN does not have a distinctive foundation and advantages in terms of development path, economic level of member states, and so on. And it still faces six crucial challenges such as increasing national trade protectionism, similar economic structures of member countries, etc. But the signing of RCEP and the steady construction of the ASEAN Community are building its path towards a common market. ASEAN is trying to practice a well-suited development path based on the uniqueness of its situation and is gradually becoming a successful regional cooperation organization.