This work investigates the failure patterns of ice cakes and floe-ice when loaded by a moving and sloping structure (ice-breaking ships and cones). In the paper, we introduce the most frequently encountered ice-infested scenarios, the main characteristics of ice-breaking ships and the predicted failure modes of floe-ice depending on the loading conditions, the structure type and the ice feature dimensions and thickness. For the simulations, a local bonded discrete element method (DEM) is used to model sea ice and its fractures. The packing of bonded spherical particles which reproduce the ice continuum can break due to ship–ice interactions and the failure modes are studied. A set of validation simulations are first carried out. A level ice sheet breaking against an installed ice-breaking cone with different slope angles is studied, and the results are compared with other DEM simulations. Then, a group of bonded DEM simulations are performed to predict the different failure modes produced when an ice-breaking ship bow contacts with ice cakes and floe-ice of different dimensions and thickness, typical in broken ice fields. Finally, the study of breaking a continuous level ice sheet is carried out by modeling with the bonded DEM an “infinite” large domain of sea ice and loaded by a single-degree-of-freedom model of an ice-breaking ship.