Conical picks are applied to rock breaking, and the cutting parameters greatly influence cutting performance and rock damage. A conical pick rock-cutting numerical simulation model and software to provide a quantitative analysis of rock damage are established to research the influence of cutting parameters on cutting force and rock damage. The research results indicated that the average peak cutting force decreases with an increased cutting angle, and the average peak cutting force increases with a decreased cutting speed. The average peak cutting force of the second conical pick increases as the distance between double conical picks increases in the process of rock-cutting with double conical picks. There is a positive correlation between the volume of rock damage, the volume of rock breaking, and the cutting force of the conical pick. The research results provide a reference for optimizing the cutting parameters of conical picks.