This chapter analyzes 17 interviews with teachers in five Sicilian lower secondary schools to explore how anti-Roma racism is simultaneously denied and reproduced. While direct contact with Roma students occasionally reduces emotional prejudice, it does not affect deeper dimensions such as anti-intimacy or low academic expectations. These limits stem from poor-quality relationships—cold, compulsory, and unsupported by institutional structures—and from stereotypes sustained by political, media, and historical imaginaries. The privileges of non-Roma students remain invisible and normalized, while Roma students are hyper-materialized through cultural and behavioral markers. Teachers’ narratives oscillate between universalist claims of neutrality and culturalist explanations of failure, reflecting both colonial legacies and contemporary discourses of whiteness. The persistence of symbolic and relational segregation demonstrates that the absence of physical segregation does not guarantee inclusion. By applying an interdisciplinary framework that integrates historical, structural, and psychological perspectives, this study pioneers a critical approach to anti-Roma racism in Italy. It argues that effective interventions must likewise adopt interdisciplinary, context-specific strategies, ensuring warm intergroup contact and embedding anti-racist practices into everyday school life.