This paper examines the combined effects of individual characteristics (such as gender, family, and migratory background) and contextual variables (including socio-economic and cultural context, school composition, tracking, and territorial distinctions) on Italian students’ academic performance. The study seeks to explore the interaction between micro- and macro-level mechanisms and their influence on educational outcomes, drawing on Coleman’s theory (1990) of collective effects. Using OECD PISA data from 2018 and 2022, this research provides a novel diachronic analysis of educational inequalities within Italy, which has received limited attention. Educational disparities at the upper secondary level stem from a mix of individual and contextual influences, such as territorial differences and school-specific factors. Previous literature has highlighted the influence of school social composition on educational achievement, while also examining the impact of family background on segregation within Italian schools (Benadusi et al., 2010; Argentin et al., 2017; Giancola and Salmieri, 2020). Italian schools reflect diverse socio-economic and cultural backgrounds shaped by regional factors, institutions, and local environments. This research applies a multilevel regression analysis to interpret inequality structures across territorial, school, and individual levels, examining disparities in reading performance to assess changes over time and post-Covid impacts on student performance.