For several years now, an increasing number of cities have been competing for the title of “European Capital of Culture”. For cities such as Glasgow (1990), Lille (2004) and Liverpool (2008), this label has been synonymous with economic renewal and urban regeneration. Relying on the singular case of Matera, a medium-sized town in southern Italy awarded twice (Unesco World Heritage in 1993 and European Capital of Culture in 2019), this study takes the reader behind the scenes of the labelling process. The study of an ongoing process is analysed from three angles: the interplay of stakeholders, urban representations and plans to transform the city. Driven by the desire to “trace” the interactions and power play at work in this labelling process, Marina Rotolo proposes an original approach that goes beyond the studies already published on the subject, traditionally focused on assessing the impact of the cultural label. This richly illustrated work draws on several disciplines (architecture, urban history, anthropology) and mobilises a wide range of unpublished sources. In a context defined by international competition and heightened rivalry between cities, where metropolises dominate, it questions the effects of labelling on the urban fabric of medium-sized towns, such as Bourges, recently nominated for European Capital of Culture 2028.