This study uses satellite imagery and geospatial data to examine the impact of floods over the main planting areas for double-cropping rice and grain crops in the middle reaches of the Yangtze River. During summer 2020, a long-lasting 62-day heavy rainfall caused record-breaking floods over large areas of China, especially the Yangtze basin. Through close examination of Sentinel-1/2 satellite imagery and Copernicus Global Land Cover, between July and August 2020, the inundation area reached 21,941 and 23,063 km2, and the crop-affected area reached 11,649 and 11,346 km2, respectively. We estimated that approximately 4.66 million metric tons of grain crops were seriously affected in these two months. While the PRC government denied that food security existed, the number of Grains and Feeds imported from the U.S. between January to July 2021 increased by 316%. This study shows that with modern remote sensing techniques, stakeholders can obtain critical estimates of large-scale disaster events much earlier than other indicators, such as disaster field surveys or crop price statistics. Potential use could include but is not limited to monitoring floods and land use coverage changes.