Urban sprawl presents a serious challenge for sustainable urban land use. Urban planning attempts to guarantee sustainable urban development and proper use of land resources. However, a large gap usually exists between planning and actual development. This paper aims to analyze the evolutionary characteristics of urban form and the spatiotemporal dynamics of urban planning from 1964 to 2013, using the case of Hangzhou, China. We proposed a framework that included remote sensing, landscape metrics, and control effectiveness indexes. The results indicated that urban planning failed to perform effectively in Hangzhou, reflected by the uncontrolled urban sprawl during all the planning periods. The low effectiveness of planning was resulted from multiple factors, including historical economic events that made expansion unexpected, functional orientation of planning which drove fragmented suburbanization, the ineffective methods for forecasting population and land use, and the influences by the market forces. The findings deepen the understanding of the impacts of urban planning, and provide references for making rational urban management decisions and sustainable urban land management.