As more people reside in cities and metropolitan areas, urban vegetation assumes an increasingly important role as one the main providers of ecosystem services in close proximity to human agglomerations. To improve the conditions for citizens and to optimise the sustainability of urban areas, the fields of landscape and urban ecology need to address the urgent priority to integrate ecological data in spatial planning, design, and management programs. With the objective to produce “actionable knowledge” for urban planning in the city of Porto (Portugal), we analyse the evolution of land cover since the mid-20th century at a fine spatial scale. Porto has followed the global trends of urbanisation, marked by a general increase in built-up and impervious surfaces that conquered the previously rural surrounding areas. This caused a severe decline in vegetation cover (especially herbaceous), as well as an increase in fragmentation and isolation of the remaining vegetation patches. These outcomes provide a detailed analysis of the city spatial dynamics, generating valuable information that can be relevant for future interventions regarding urban landscape change at a local scale, the most relevant for planning.