tIn the past few decades, urbanisation has become a major phenomenon in European cities, thus repre-senting one of the key human land cover changes with socio-economic and environmental impacts. In theLisbon metropolitan region it is estimated that 17% of natural and farmland have been transformed intoartificial areas. Since the end of 1990s, specific EU guidelines have been issued to contain urban sprawland preserve agricultural land. Spatial planning in Portugal obviously is integrating these assumptionsinto the statutory land-use master plans. But what is the performance of this land use planning systemregarding land cover evolution itself? Based on the Lisbon metropolitan region (LMR), one of the majorareas of urban growth in Portugal, we examine spatio-temporal land cover patterns between 1990 and2007 by integrating cross-matrix analysis, spatial metrics, and gradient analysis. Additionally, we over-lay these land cover dynamics with municipal master plans that regulate land development in order toassess the compliance levels of this land-use regulatory system. Results indicate that: artificial areas aregrowing by coalescence and/or by scattered development along an urban–rural gradient; agriculturalland is reducing and fragmentation is increasing to enlarge peri-urban spaces; there are high levels ofconversion of agricultural land into urban land in protected areas, thus showing a lack of compliance tothe land use regulatory system visible in the existing gaps between the original land-use assignments ofthe master plan and the actual developments.