Dubai, a city synonymous with multiple world-record breaking achievements in terms of architecture, rapid growth, and advancement in several fields. A definitive force in the region that aims to not only excel ahead of its neighbors, but lead amongst the world's best. The next ambitious project is hosting the World Expo 2020 that will utilize modern technology and design in daily transactions and innovative infrastructure to fuel the city's movements. There are many challenges and concerns that are immediately apparent when revisiting the long-term effects of previous World Expos through the years. The purpose of this scientific study is to identify and to anticipate these challenges while ideating possible solutions for them at the same point in time. The following methods were used for the research at hand: Identification, analysis and comparison of most relevant secondary data sources within the research areas of event and sustainability management. In addition, depth interviews with academics that are well-versed within the field of sustainability as well as with individuals working within Expo 2020 were conducted. The research presents an overview of key learnings from previous World Expos along with what additional novel and creative measures have been introduced in the blueprint for Expo 2020 and its future. The scope of this article is limited to an analysis of past mega events while external circumstances may vary in 2020 due to dynamic and fast changing external environments. Additionally, interview bias was reduced to a minimum but cannot be fully eliminated.