Diversity in Higher Education system has been a central topic for both scholars and policy-makers for decades. Several studies have investigated how to measure diversity and the nature of its determinants so far; however, contradictory empirical evidence has emerged. This paper contributes to this literature by adopting a methodological approach that starts from the analysis of positioning paths of Higher Education Institutions (HEIs) in order to explore the diversity of HE systems. A comprehensive quantitative analysis performed across two HE systems over time shows how detecting the positioning of HEIs can provide information that an analysis of diversity at the level of the entire system might hide, in particular (I) if and how compliant and distinctiveness are concurrently displayed (II) in which dimensions positioning shifts are more likely to occur and (III) which groups of HEIs influence more the level of diversity in a HE system.