|Abstract:||In today’s world, the emergence of underdog stories, especially in the sports community, is becoming increasingly frequent. One of those ‘Cinderella’ stories is of the University of Illinois Chess team. Despite having a much lower ranking than the chess teams of elite universities (like Webster University, University of Texas at Dallas), the U of I Chess Team qualified for the President’s Cup (also known as the Final Four of Chess) against all odds. This led me to the question: how exactly do underdogs (like the U of I Chess Team), who are not even remotely comparable to the star-studded heavyweights (like the chess teams of Webster University, University of Texas at Dallas, etc.), manage to beat them?