Critical research and analysis of the link between urban development, urban law and judicial decisions in the cities of Sub-Saharan Africa is limited. Drawing on lessons from Maseru, Lesotho, this paper advances a critical analysis of the link between urban law, judicial decisions and urban development. The paper suggests that Lesotho's urban land law, the Land Act of 1979 (LA 1979) has two facets. The first facet is that LA 1979 is exclusionary because in terms of access to urban housing land, it discriminates between individuals on the basis of their socioeconomic wealth and access to those who wield state power. The second facet is that LA 1979 is ostensibly empowering, as it has permitted urban residents who have acquired urban housing land through informal delivery processes to challenge state attempts to appropriate their land without compensation. The paper notes that the first facet has remained significantly unchanged since the enactment of LA 1979 in June 1980, while the second facet only emerged in 1993, when constitutional rule was reinstated after nearly 23 years of autocratic regimes. The paper concludes that the reinstatement of constitutional rule in 1993 has permitted the courts to reinterpret the rules-of-the-game in ways that have privileged the rights of ordinary urban residents over those of the state. In the process, the judiciary has established solid foundations for transparent, accountable, and participatory urban planning and governance, a culture that the planning profession in Lesotho is yet to internalise.