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As an “index case” of Third-Wave democracies facing existential threat, Taiwan’s elections entail important implications for study in comparative politics and international relations. In 2008, three important elections help define the course of Taiwan’s democratic development and its relationship with China: the January legislative election, the March presidential election, and a controversial referendum on Taiwan’s United Nations entry. This article employs game theory to analyze the impact of Taiwan’s 2008 elections on cross-strait relations. It develops an “election game” by examining each principal player’s preferences regarding each election. It analyzes Beijing’s possible reaction to the potential outcomes, and then examines the actual election outcomes against the model and offers observations on the prospect of cross-strait relations. Overall, the model predicts that cross-strait relations after the 2008 elections will present a historic opportunity, which can be seized or squandered, depending on political leadership.