Comparative research on school-to-work transitions mainly focused on country differences, examining the variation in institutional design and its impact on shaping youth labour market outcomes. The field has been dominated by a sort of methodological nationalism assuming nation states as homogeneous objects of comparison, while the territorial variations in youth transitions among sub-national territories have been less explored, notwithstanding their potential impact on life chances. In this article, we look at the outcomes of transitions in EU regions, comparing regional configurations of school-to-work transitions and their change over time. Is it possible to identify differences among groups of regions? To what extent do these patterns change over time? In order to answer these questions, we construct and analyse a longitudinal and systematic set of indicators that combine regional aggregated outcomes of transitions from education to work and regional contextual traits at the Nomenclature of Territorial Units for Statistics level 2 for the period 2007–2019. We perform two cluster analyses to describe regional differences and trends over time. The findings provide novel insights into the characteristics and patterns of an unequal geography of youth opportunities in Europe.