The Kanto plain that is the largest depositional plain in Japan has the largest urbanized area called Tokyo Metropolitan Area. This plain has experienced extensive groundwater withdrawals for water resources and human induced disasters such as land subsidence in the process of urbanization. Japanese national government and local governments have monitored groundwater levels and settlement of ground surface for about half a century. These data are useful not only for the prevention of these disasters but for the evaluation of the change of groundwater flow beneath the urbanized area. However, few hydrological and hydrogeological studies about the change of groundwater flow in this plain have been conducted until now except for several studies which were limited in areal extent. In this paper, changes of the distribution of hydraulic heads in the central part of this plain are discussed using the long-term groundwater level observation data to evaluate the change of groundwater flow. The temporal changes in the distribution of hydraulic heads in a major confined aquifer (the second aquifer) and the areal extent of the urbanized area for approximately 50 years can be summarized as follows. In the latter half of the 1950s, urban area was limited in the southern region of the study area and hydraulic head gradually declined from the northwest to the southeast in the study area. After the 1960s, urban area extended toward the north and groundwater in the northern part was largely abstracted until the 1980s. As a result, hydraulic heads in this area markedly declined. On the other hand, hydraulic heads in the southern part began to rise because of the restriction of groundwater withdrawals. In recent years, low hydraulic head area has been formed from the northern region to the central region. These results suggest that the groundwater flow which was affected by urbanization (groundwater withdrawals) has continued to change over several decades, even after the regulation of withdrawals, and hence, the continued monitoring of the groundwater environment is important for the sustainable use of groundwater resources.