Woodlands and savannahs provide essential ecosystem functions and services to communities. On the African continent, they are widely utilized and converted to subsistence and intensive agriculture or urbanized. This study investigates changes in land cover over four administrative regions of North Eastern Namibia within the Kalahari woodland savannah biome, covering a total of 107,994 km2. Land cover is mapped using multi-sensor Landsat imagery at decadal intervals from 1975 to 2014, with a post-classification change detection method. The dominant change observed was a reduction in the area of woodland savannah due to the expansion of agriculture, primarily in the form of small-scale cereal and pastoral production. More specifically, woodland savannah area decreased from 90% of the study area in 1975 to 83% in 2004, and then increased to 86% in 2014, while agricultural land increased from 6% to 12% between 1975 and 2014. We assess land cover changes in relation to towns, villages, rivers and roads and find most changes occurred in proximity to these. In addition, we find that most land cover changes occur within land designated as communally held, followed by state protected land. With widespread changes occurring across the African continent, this study provides important data for understanding drivers of change in the region and their impacts on the distribution of woodland savannahs.