This paper focuses on the functioning and territorial organization of the Italian and Canadian health systems. Though to a different extent, health care governance in these countries is decentralized. Decentralization is a term rich of conceptual and empirical meaning, and can designate static and dynamic processes. The distinction between decentralized and centralized systems, as well as between federal and unitary states, is a matter of degree, rather than a fully-fledged dichotomy. The article explores the dynamics of decentralization in health care, investigating why and how the territorial organization of health systems changes or remains stable. Through a comparative historical analysis of the institutional arrangements and reform trajectories in light of the decentralization process, and distinguishing between three dimensions of decentralization (political, administrative and fiscal), I aim at reconstructing and tracing the process through which distinct patterns of health system decentralization have occurred over time in the selected countries.