In the past two decades, severe drought has been a recurrent problem in Iraq due in part to climate change. Additionally, the catastrophic drop in the discharge of the Tigris and Euphrates rivers and their tributaries has aggravated the drought situation in Iraq, which was formerly one of the most water-rich nations in the Middle East. The Kurdistan Region of Iraq (KRI) also has catastrophic drought conditions. This study analyzed a Landsat time-series dataset from 1998 to 2021 to determine the drought severity status in the KRI. The Modified Soil-Adjusted Vegetation Index (MSAVI2) and Normalized Difference Water Index (NDWI) were used as spectral-based drought indices to evaluate the severity of the drought and study the changes in vegetative cover, water bodies, and precipitation. The Standardized Precipitation Index (SPI) and the Spatial Coefficient of Variation (CV) were used as meteorologically based drought indices. According to this study, the study area had precipitation deficits and severe droughts in 2000, 2008, 2012, and 2021. The MSAVI2 results indicated that the vegetative cover decreased by 36.4%, 39.8%, and 46.3% in 2000, 2008, and 2012, respectively. The SPI’s results indicated that the KRI experienced droughts in 1999, 2000, 2008, 2009, 2012, and 2021, while the southeastern part of the KRI was most affected by drought in 2008. In 2012, the KRI’s western and southern parts were also considerably affected by drought. Furthermore, Lake Dukan (LD), which lost 63.9% of its surface area in 1999, experienced the most remarkable shrinkage among water bodies. Analysis of the geographic distribution of the CV of annual precipitation indicated that the northeastern parts, which get much more precipitation, had less spatial rainfall variability and more uniform distribution throughout the year than other areas. Moreover, the southwest parts exhibited a higher fluctuation in annual spatial variation. There was a statistically significant positive correlation between MSAVI2, SPI, NDWI, and agricultural yield-based vegetation cover. The results also revealed that low precipitation rates are always associated with declining crop yields and LD shrinkage. These findings may be concluded to provide policymakers in the KRI with a scientific foundation for agricultural preservation and drought mitigation.