Abstract: Remote sensing can provide near real-time and dynamic monitoring of drought. The drought severity index (DSI), based on the normalized difference vegetation index (NDVI) and evapotranspiration/potential evapotranspiration (ET/PET), has been used for drought monitoring. This study examined the relationship between the DSI and winter wheat yield for prefecture-level cities in five provinces of eastern China during 2001–2016. We first analyzed the spatial and temporal distribution of droughts in the study area. Then the correlation coefficient between drought-affected area and detrended yield of winter wheat was quantified and the impact of droughts of different intensities on winter wheat yield during different growth stages was investigated. The results show that incipient drought during the wintering period has no significant impact on the yield of winter wheat, while moderate drought in the same period can reduce yield. Drought affects winter wheat yield significantly during the flowering and filling stages. Droughts of higher intensity have more significant negative effects on the yield of winter wheat. Monitoring of droughts and irrigation is critical during these periods to ensure normal yield of winter wheat. This study has important practical implications for the planning of irrigation and food security.