With the deepening of the Belt and Road Initiative (BRI), many Chinese have been dispatched to Southeast Asian countries to participate in technical support and management. However, there are no OCE schools locally that can provide educational resources for their children. The decision of whether to invest in overseas Chinese-OCE has become a challenge for Chinese education groups. In this paper, the authors put forward an evolutionary game analysis scheme to study the OCE investment decisions among host country governments, students, and Chinese enterprises. The simulation results show that (1) the government's subsidy is always helpful to Chinese enterprise, especially at the beginning stage, (2) applying a soft strength of positive execution and combining with other methods could encourage the enterprise at the beginning and regulate the market later on, and (3) high strength of high support of government for the educational infrastructure is a win-win method for both students and the enterprise. Some managerial insights and suggestions are proposed based on these results.