Railway ballast particles undergo significant amount of breakage under repeated train load. Breakage of ballast particles, especially highly angular fresh ones causes an increase in settlement contributing to track degradation. The quantitative analysis of the influence of breakage on the stress-strain properties of ballast can be performed either experimentally or numerically. Numerical modeling has the advantage of simulating ballast breakage subject to various types of loading and different boundary conditions for a range of material properties. In this paper, ballast breakage under cyclic loading is simulated using a 2-D discrete element method (DEM) utilizing the software PFC2D. A new subroutine is developed and incorporated in the PFC2D analysis to study ballast breakage and to quantify breakage in relation to particle size distribution. The influence of confining pressure on both breakage and permanent deformation is also studied and compared with laboratory observations. The findings of this paper provide an insight into the true ballast behavior under cyclic loading and are expected to assist railway practitioners for developing suitable design criteria for track stability.