This project is centered around a decade-old video game called League of Legends, which is one of the most popular video games in esports. Due to its nature of being a complex team-based strategy game, intuitive human predictions of the game’s outcome are relatively unreliable. Many approaches have been adopted to assist intuitive human predictions in traditional team-based sports, such as the Least Squares Method and various supervised machine learning algorithms. These methods have been significantly outperforming human predictions. The objective of this research is, hence, to test whether the predictive models generated using these methods can achieve a similar level of reliability in a more complex game like League of Legends.