This study investigates long-term landscape transformations (1949-2016) in urban Rome, Central Italy, through a spatial distribution of seven metrics (core, islet, perforation, edge, loop, bridge, branch) derived from a Morphological Spatial Pattern Analysis (MSPA) analyzed separately for seven land-use classes (built-up areas, arable land, crop mosaic, vineyards, olive groves, forests, pastures). A Principal Component Analysis (PCA) has been finally adopted to characterize landscape structure at 1949 and 2016. Results of the MSPA demonstrate how both natural and agricultural land-uses have decreased following urban expansion. Moreover, the percent 'core' area of each class declined substantially, although with different intensity. These results clearly indicate ‘winners’ and ‘losers’ after long-term landscape transformations: urban settlements and forests belong to the former category, the remaining land-use classes (mostly agricultural) belong to the latter category. Descriptive statistics and multivariate exploratory techniques finally documented the intrinsic complexity characteristic of actual landscapes. The findings of this study also demonstrate how settlements have expanded chaotically over the study area, reflecting a progressive 'fractalization' and inhomogeneity of fringe landscapes, with negative implications for metropolitan sustainability at large. These transformations were unable to leverage processes of settlement and economic re-agglomeration around sub-centers typical of polycentric development in the most advanced socioeconomic contexts.