Cricket is the second most popular sport in the world with a significant presence in Commonwealth countries. Despite its popularity, cricket is underrepresented in the literature, especially in the domain of simulation. Simulation in cricket is challenging because of its complexity, dynamic nature, and data scarcity. In this research, we develop a simulation mechanism for cricket using machine learning techniques. The construction of the simulator is based on the availability of a detailed dataset from Cricket Australia. We employ machine learning to predict the outcome of a “delivery”, the core element of gameplay, which can further be utilized for scorecard generation and match simulations. Our simulator’s potential is demonstrated by employing it to determine the optimal batting position of a given batter in a team in Twenty20 cricket. Additionally, we develop an interactive web platform to enable direct interaction with the simulator and the tool for optimizing batting positions.