Numerical simulations have been conducted to model the deformation, damage, and fracture growth caused by the plunge of a spherical drill bit insert into a brittle rock. The deformation of the rock, which is initially homogeneous and isotropic, is modeled using the finite element method. Fracture geometry evolves as a function of fracture growth, and the rock domain is continuously re-meshed to capture this geometric change. Contact forces are applied radially over the contact area as a function of the depth of the plunge. A series of simulations is presented, having varying initial flaw distributions, and which capture the fracture pattern formation during the progressive indentation of the insert into the rock. The ensuing patterns depict the formation of horizontal and Hertzian fractures. A large fracture density is created around the contact area. The complexity of the internal fracture structure is less apparent at the surface of the deformed rock, as compared to the internal fracture pattern. Fracturing leads to the formation of surface chips in the form of tilted elliptical domains parallel to the rock surface. Early stages of chipping are not always apparent from the fracture pattern at the surface of the rock. Results are in good agreement with experimental observations.