This chapter reviews the historical evolution of Olympic urban planning, examining how the Games have driven urban regeneration and boosted global competition. While the Games have showcased transformative successes, they have also faced criticism for socio-economic and environmental consequences, including displacement, gentrification, and “white elephant” projects. The chapter further explores the emergence of sustainability as a guiding principle in Olympic planning, highlighting milestones such as the inclusion of environmental responsibility in the Olympic Charter and the development of legacy-focused initiatives. Despite these advancements, issues of greenwashing, socio-spatial inequities, and escalating costs have persisted, fostering public opposition and challenging the Games' sustainability. This chapter thus contextualises Olympic Agenda 2020 within broader urban planning debates, focusing on its aim to address these critiques by reforming candidature processes, prioritising sustainability, and reducing costs. It concludes with a review of the academic discourse surrounding the Agenda, which reveals mixed perspectives. Scholars recognise its innovations but critique its limited enforceability, ambiguous sustainability metrics, and insufficient stakeholder engagement. By framing these issues, the chapter situates this research within ongoing discussions about the Olympic Games’ evolving role in urban planning and sets the foundation for assessing the Agenda’s implications and practical impacts in subsequent chapters.