Land use decisions induce legacies that affect the welfare of future generations. Here, we present a spatial modeling approach for quantifying how past land use decisions influence provision of multiple ecosystem services (ESs) based on different land use trajectories. We modeled the effect of past land use changes on water regulation, soil protection and habitat quality in southern Spain, one of the most transformed areas of the Mediterranean region. We demonstrate a measurable influence of antecedent land use changes on the capacity of a given land use to provide ESs, and that the effect size can vary among different services and land use trajectories. Our results suggest that afforestation programs may decrease habitat quality but not alter soil protection, depending on whether the previous land use was cropland or shrubland. Although it is well-established that land use legacies motivated by past land decisions are ubiquitous and crucially important for effective landscape management, the question of how the magnitude and spatial distribution of ES supply vary under different land use trajectories remains unknown. Our approach enables quantification of how land use legacy affects ecological processes that underpin ES capacities at a regional scale, which will allow land managers to develop more accurate landscape planning strategies for preserving ESs.