Drought is a complex phenomenon that has severe impacts on the environment. Vegetation and its conditions are very sensitive to drought effects. This study aimed to monitor and assess the drought severity and its relationships to some ecological variables in ten districts of Erbil Governorate (Kurdistan Region), Iraq, throughout 20 years (1998-2017). The results revealed that droughts frequently hit Erbil throughout the study period. The Landsat time-series-based on Vegetation Condition Index (VCI) significantly correlated with precipitation, Digital Elevation Model (DEM), and latitude. Extreme VCI-based drought area percentages were recorded in 1999, 2000, 2008, and 2011 by 43.4%, 67.9%, 43.3%, and 40.0%, respectively. The highest crop yield reduction in the study area occurred mainly in 2000, 2008, and 2012 due to low precipitation rates. These results reveal the capability of the VCI for drought characteristics and highlighting relationships with some ecological variables, which provide vital information to the decision-makers, environmental, and economic sectors.