A numerical approach to particle breakage is applied using the Rock Failure Process Analysis code, RFPA2D. The numerical tool is validated by simulating the Brazilian test with a two-dimensional disk sample. Then two irregularly shaped particles with an exact geometry and exact mechanical properties are numerically modelled to investigate their breakage behaviour under unconfined and confined loading conditions. The numerical results indicate that the dominant mode of failure is catastrophic splitting and progressive crushing, which mainly depends on the loading conditions with respect to confinement. The analysis of the load-displacement curves obtained from the simulations suggests a brittle-ductile transition between the two cases. The lateral constraint increases the initial stiffness and the maximum breakage strength of the particle. Most of the energy released during the failure process comes from the crushing of highly stressed areas, particularly, in the vicinity of the contact points where a crushed zone forms. It is also found that the particle shape governs the breakage strength in addition to the material properties themselves, and that the heterogeneity of the particles governs the fracture propagation paths.