Amid the vigorous development of the high-speed rail (HSR) network, local governments in China generally consider the construction of HSR as a crucial task in their regional development strategies. Currently, most provincial capitals and prefecture-level cities in the eastern and central regions of China already have operational HSR services. This study aims to examine a key question: has the objective of local governments to promote urban development through the construction of HSR been effective? The research selects cities along the Beijing–Shanghai, Beijing–Guangzhou, and Harbin–Dalian HSR lines as the study subjects. Based on the principles of proximity and similarity, cities with operational HSR and those without are chosen as the experimental group and the control group, respectively. Following the double difference (difference-in-differences) approach, an advantage index is proposed to systematically evaluate the impact of HSR operation on urban development from three dimensions: population aggregation, economic development, and expansion of construction land. Furthermore, the evaluation results are systematically clustered to identify city types that exhibit different promotional effects in various dimensions. The research findings indicate the following: (1) The promotion effect of HSR on the development of small to medium-sized cities is more reflected in economic growth and construction land growth. (2) The promotion effect of HSR on the development of large cities is more reflected in the growth of the employment population. (3) For smaller or economically less-developed cities, HSR may be detrimental to the aggregation of resident and employment populations. (4) Cities with moderate size and good economic development have the opportunity to use HSR to promote population aggregation. On this basis, combined with the findings above, strategies to promote the coordinated development of high-speed rail construction and urban systems are discussed.