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This paper compares the security environment and challenges surrounding the Sochi 2014 Winter Olympics and the 2018 World Cup to be held in Russia. In many ways these twin events form bookends to the current era of international relations, as the conflict in Eastern Ukraine rose straight out of the 2014 Winter Olympics. The paper systematically recounts the different security environments for the two events and asks whether the approach Russia took to combat security challenges in 2014 will be successful in 2018. The paper argues that Russia’s 2014 approach to providing security is unlikely to be successful in securing the 2018 event due mainly to the changed nature of the threat, but also to the large scale of the World Cup.