The unprecedented increase in population and urbanization dynamics, particularly without the requisite road infrastructure on the African continent, necessitates a more contextual understanding of the interaction between urban expansion and transportation in its cities. The study used Landsat and Google Earth, two readily available data in a resource-constrained context, and population data from 1999 to 2018 to estimate the interactions between roads stock, urban size and corresponding population changes in Akure, a mid-sized capital city in Nigeria, with substantial federal road connectivity. The results suggest strong positive relationships among all the variables of interest. At α = 10%, an increase in road stock causes a significant ( p = 0.064) increase in population. The study reveals a heavier road density as the city expanded, slightly reduced from the core, with an increased stock of roads toward the periphery. These findings could significantly inform how cities evolve and can guide urban and transportation planners on complementary road infrastructure for growing cities. The study recommends that, irrespective of the political dispensation, the government could increase connective and motorable road stock toward the periphery each fiscal year, with promises of sustainability and resilience in the urban system despite the ever-increasing population.