The North China Plain (NCP) is one of the main agricultural areas in China. However, it is also widely known for its water shortages, especially during the winter wheat growing season. Recently, climate change has significantly affected the water environment for crop growth. Analyzing the changes in the water deficit, which is only affected by climate factor, will help to improve water management in the NCP. In this study, the Decision Support System for Agrotechnology Transfer (DSSAT) was used to investigate the variations in the water deficit during the winter wheat growing season from 1961 to 2010 in 12 selected stations in the NCP. To represent the changes in the water deficit without any artificial affection, the rainfed simulation was used. Over the past 50 years, the average temperature during the winter wheat growing season increased approximately 1.42 °C. The anthesis date moved forward approximately 7-10 days and to late April, which increased the water demand in April. Precipitation in March and May showed a positive trend, but there was a negative trend in April. The water deficit in late April and early May became more serious than before, with an increasing trend of more than 0.1 mm/year. In addition, because the heading stage, which is very important to crop yield of winter wheat, moved forward, the impact of water deficit in late April was more serious to crop yield.