The sailboat game is popular in supply chain management teaching. In the game, students play different roles in a supply chain and try to achieve better performance in terms of minimizing costs, while gaining knowledge in production processes, quality management, and inventory management. Despite its popularity, how the sailboat game is beneficial to different student groups is unclear. The current paper documents two sailboat games held in two cities, Macau and Zhuhai, respectively. We distribute anonymous questionnaires after the two games and compare the responses. Through the comparison, we contribute to the knowledge base of management education in the following ways. First, we identify statistically significant differences between students in the two cities, which provide implications for implementing the game in various cultural contexts, as well as the distinctions between the two education systems. Second, we collect comments from students, which hint at possible improvements of the game in the future.