This paper attempts to describe and analyze the development and reforms of secondary education in Hong Kong and Shanghai over the past 25 years. Comparing the two cities is useful in constructing a spectrum of possibilities on the one hand, and identifying some common themes in the development of secondary education on the other. The commonalities and differences, the experiences and lessons, should shed light on similar reforms in other parts of the world. Section 1 provides the background in which both cities launched their respective education reforms. Section 2 provides contextual descriptions of the two education systems. Section 3 illustrates changes in the workplace in both Hong Kong and Shanghai. Section 4 summarizes the challenges facing education in Shanghai and Hong Kong. Section 5 examines the efforts at reform in both systems, concentrating on secondary education. Section 6 revisits the purpose of secondary education in the context of: (a) almost universal attendance in secondary education in both cities; (b) few job opportunities for fresh secondary graduates; and (c) a majority of the population having to undertake lifelong learning. Finally, Section 7 concludes by stating that there must be a reassessment of the nature, goals, and contents of secondary education. Both cities have done tremendous work in this direction, most significantly in the reform of the curriculum, where the general tendency is to move away from fragmented feeding of specific knowledge toward establishing learning experiences that have long-term significance.