The Upper Mesopotamia region, also called Jezira, is a rural plain split by the Syrian-Turkish border. The region was subject in the last three decades to prominent changes to the land cover, mainly due to the vast development of irrigation projects from both sides of the border. The research aims at detecting differences to the trend of land cover changes between the adjacent territories.The study makes use of Remote Sensing change detection techniques, applied to Landsat satellites images from 1984 to 2015. Considering the arid to semi-arid climate characteristic of the region, the analysis takes into consideration the local water management policies and drought events.As an output, the research quantifies the direction of the surface changes occurred in several intermediate times, underlining the differences across the border. The study highlights how surrounding conditions can intensify the impact of drought periods, such as the 2006–2010 drought that severely affected the Syrian territory.