Drought is a common event in Iraq’s climate, and the country has severely suffered from drought episodes in the last two decades. The Kurdistan Region of Iraq (KRI) is geographically situated in the semi-arid zone in Iraq, whose water resources have been limited in the last decades and mostly shared with other neighboring countries. To analyze drought impacts on the vegetation cover and the land surface temperature in the KRI for a span of 20 years from 1998 to 2017, remote sensing (RS) and Geographical Information Systems (GIS) have been adopted in this study. For this study, 120 Landsat satellite images were downloaded and utilized, whereas six images covering the entire study area were used for each year of the study period. The Normalized Difference Vegetation Index (NDVI) and Land Surfaces Temperature Index (LST) were applied to produce multi-temporal classified drought maps. Changes in the area and values of the classified NDVI and LST were calculated and mapped. Mann–Kendall and Sen’s Slope statistical tests were used to assess the variability of drought indices variation in 60 locations in the study area. The results revealed increases in severity and frequency of drought over the study period, particularly in the years 2000 and 2008, which were characterized by an increase in land surface temperatures, a decrease in vegetation area cover, and a lack of precipitation averages. Climate conditions affect the increase/decrease of the vegetated cover area, and geographical variability is also one factor that significantly influences the distribution of vegetation. It can be concluded that the southeast and southwestern parts of the KRI were subjected to the most severe droughts over the past 20 years.