Looking at gambling from a mathematical point of view, it is a stochastic problem that can be evaluated and analyzed through random simulation. In this paper, we give the calculation process of gambler’s bankruptcy probability through a specific two-person gambling game, and then use MATLAB to randomly simulate the gambling process to get the simulated bankruptcy probability. In addition, Monte Carlo simulation is used to simulate three kinds of common gambling systems: the simple betting system, the double betting system and the D ‘Alembert’s system. Their winning rate or bankruptcy rate are also calculate respectively. According to the simulation results, this paper analyzes and summarizes the characteristics of gambler friendly gambling system represented by Labouchere system. However, even with the optimal gambling strategy at the fairest bets, gambler who gamble with casinos can end up bankrupt because of the law of large numbers.