Drought is a natural hazard that significantly impacts economic, agricultural, environmental, and social aspects and is characteristic of Iraq’s climate, particularly the Iraqi Kurdistan Region (IKR). For studying the spatiotemporal characteristics of drought severity in the IKR, a time-series of 120 Landsat images (TM, ETM+, and OLI sensors) over twenty years (1998-2017) was assembled. Twenty separate mosaics of six Landsat scenes were used to derive the Vegetation Condition Index (VCI). The VCI index was employed to capture the drought severity in the study area. Results revealed that 1999, 2000, and 2008 were the most severe drought years. The results also indicated that severe droughts increased by 29.1%, 25.0%, and 26.9 through 1999, 2000, and 2008, respectively. Furthermore, a drop in precipitation averages occurred in the two years and significantly reduced the VCI values. Statistical analysis exhibited significant correlations between the VCI and each precipitation, and crop yield was 0.810 and 0.478, respectively. It can be concluded that the IKR experienced severe to extremely severe agricultural droughts, which caused significant reductions in crop yields, particularly in 2000 and 2008.