In this research, we propose an option sell-side trading strategy with a fixed stop-loss mechanism according to the concept of money management. In our strategy, the maximum profit and loss are fixed through the introduced stop-loss mechanism to reduce the risk of excessive losses. We apply the traditional statistical approach and random forest algorithm to estimate the win-rate and visualize the win-rate distribution through Heatmap and the profitable trading range filtered by win-rate threshold could be obtained. The effective indicator, Accuracy, precision, and AUC-ROC curve are selected to evaluate the performance of the predictive model proposed in this research. The experimental result illustrates that the random forest predictive model to our strategy demonstrate outstanding performance (highest precision reached 0.9) which outperform the traditional statistical approach and could achieve the objective of implementing money management and risk management to option trading strategy.