The City of Sydney’s urban planning philosophy and practice experienced fundamental changes in the 1980s and 1990s. In the post-World War decades, Sydney’s urban planning was characterized by a laissez faire tradition which exempted any attempt to plan and control the city. Furthermore, this laissez faire context was interrelated with the conflicts of planning powers between the New South Wales State Government and its agencies, and the Sydney City Council. However, this ad hoc planning approach and conflict-ridden planning politics between tiers of governments appeared to give way to a converged recognition of the importance of planning intervention and concerted planning actions among major stakeholders in the pursuit of a global Sydney in the 1980s and the 1990s. This article attempts to address two questions of the urban planning transformation in Sydney: (1) how did the transformation occur? and (2) what were the thematic patterns of the transformation? This article describes Sydney’s historical planning background, makes a content analysis of benchmark strategic plan documents – The City of Sydney Strategic Plan (1971–1983) and Central Sydney Strategy (1988), and narrates the planning practices in the pre-Olympics 2000 years. This article finally concludes the thematic patterns of urban planning transformations in Sydney in the 1980s and 1990s: the intergovernmental consensus on visioning and planning for a global Sydney, the thematic planning transformations including the emergence of entrepreneurial planning with the prominence of economic planning, the neutralization of the social planning, and the emphasis on urban design in the physical planning.