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The city of Riyadh, Saudi Arabia has experienced rapid population growth and urban expansion over the past several decades. Due to such growth, the capital city faces many short and long-term social and environmental consequences. In order to monitor and mitigate some of these consequences, it is essential to examine the past changes and historical growth of the city. It is also essential to measure its urban sprawl over the past few decades. The objective of this study is to fulfil these goals. It does so by first examining the historical growth of the city of Riyadh. To do so, Landsat data over the past two and half decades are classified using a combination of supervised and unsupervised classification techniques. Based on the classification results, the study then uses Shannon’s Entropy to measure the urban sprawl in the city. The results show that from 1990-2009, the urban built-up area of the city has increased by 90% in the western, south-eastern, and northern parts. The Shannon’s entropy values show that the city is dispersing towards the outskirts of the city. The results from this study will assist city planners and government officials to plan, reduce, and perhaps mitigate some of the social and environmental consequences and enable the growth of the city in a sustainable manner in the near future.