The spread of Xylella fastidiosa since 2013 in the Mediterranean olive groves of the Apulia region has modified the landscape. The aims of this research are focused on the analysis of its effects on the following: (1) Landscape multifunctionality supported by olive groves in terms of landscape service provision; (2) The functional relations among the main Mediterranean land covers in terms of landscape service supply and demand. (3) The landscape fragmentation at different spatial scales. The landscape has completely changed, mainly in those land covers that, in the past, acted as stabilizing factors (croplands and olive groves), which has been replaced by grasslands in 2021. The main effects of Xylella fastidiosa were on the multifunctionality of olive grove landscape in terms of food production, water regulation, carbon sequestration, and pollination, as well as on landscape cultural value. Ecosystem service supply is mainly related to olive groves, tree covers, shrublands, and wetlands. The province of Lecce showed the highest fragmentation, as demonstrated by the number of patches, the mean patch area, and the DIVISION metric, while the province of Brindisi was the least fragmented, with a DIVISION metric similar in 2011 and in 2021. The multiscale assessment of “olive groves” fragmentation has helped in better analyzing the effect of its spatial configuration on the provision of landscape services and in identifying the right spatial scale for each landscape service provision. It is essential to analyze landscape service flow to enlarge the understanding of the ways in which their supply is maintained through a landscape regeneration policy toward the socio-economic–ecological recovery.
