A numerical technique that couples the distinct-element and boundary-element methods was developed to simulate a granular soil deposit as a two-dimensional, circular disk assembly. A series of simulated penetration tests of a 60° apex angle cone was performed in normally consolidated and overconsolidated disk assemblies. The simulations allowed the cone penetration mechanisms to be evaluated from microscopic as well as the conventional, continuum mechanics points of view. Results show that the soil loading history can affect the characteristics of the soil failure mechanism and dilatancy. Lateral stress measurement behind the cone base is not sensitive to soil loading history. Finer particles appear to experience higher contact stresses and hence are more likely to be crushed by the cone penetration.Key words: cone penetration, sand, shear strength, loading history, distinct-element method.