Agricultural drought occurs when inadequate soil moisture, caused by prolonged precipitation deficiency, significantly reduces crop yields. Corn and soybeans, vital to the U.S. agricultural sector and making up 90% of Iowa’s crop production, are highly vulnerable to drought. This study quantified widely used drought indicators and their relationship with corn and soybean yields from 2000 to 2022 to identify the most effective indices for predicting crop productivity. Meteorological and satellite-based drought indices, including the Standardized Precipitation Index (SPI), Standardized Precipitation-Evapotranspiration Index (SPEI), Palmer Drought Severity Index (PDSI), Evaporative Demand Drought Index (EDDI), Crop Moisture Index (CMI), and Normalized Difference Vegetation Index (NDVI), were analyzed alongside USDA crop yield data. Soybean yields showed strong positive correlations with SPI-6, SPI-12, SPEI-6, and SPEI-12, indicating these indices are reliable predictors of soybean productivity. Conversely, corn yields were negatively correlated with EDDI, highlighting corn’s higher susceptibility to severe drought conditions than soybeans. The Palmer Drought Severity Index (PDSI) showed stronger correlations with soybean yields over time, reflecting the crop’s reliance on sustained moisture. These findings emphasize that soybeans are more resilient to longer-term moisture deficiencies, whereas corn is more sensitive to short-term droughts. The analysis provides valuable insights for drought relief planning, agricultural decision-making, and proactive strategies for managing drought impacts. The results can inform the development of resilient farming practices and policies, ensuring sustainability in agriculture under changing climate conditions.