Abstract: The aim of this paper is to investigate how and to what extent the provision of major open spaces has been integrated (or not) into the metropolitan planning process in Sydney over the last 60 years. There is a focus on three specific dimensions of this history: roles and influence of various agencies responsible for the implementation of open space; shifting values and concepts which influenced delivery of open space; and comparison of proposals for significant regional greenspaces against the parks and open spaces that eventuated. The analysis is based primarily on a review of statutory metropolitan planning strategies and annual reports of state planning departments and authorities. It is framed across three distinct periods of urban planning in Sydney: 1940s—1960s (a period framed by two robust strategic plans when the foundation of a metropolitan green web was activated); 1960s—1980s (implementation of 1968 strategic corridor thinking through to emergence of sustainability concerns in policy-making), and 1990s to the present (from early concerns for climate change through to the multivalent notion of green infrastructure).