Moisture is detrimental to pavement performance. This is especially evident during high intensity rainfall events, where it is common to observe rapid deterioration of flexible pavement systems. Both experimental and numerical studies have evaluated the impact of moisture on pavement deterioration. However, these have not accurately defined the adhesive and cohesive failure at aggregate scale. A three-dimensional (3D) finite element model is developed with non-linear material properties based on realistic aggregate geometry. Boundary condition are obtained from finite element models of a pavement system under repeated dynamic heavy vehicle axle wheel loading. The tensile stress is measured within the asphalt and at the aggregate-asphalt interface. Results show that cohesive film failure may occur at 14,946 loading cycles at several locations where the film thickness is reduced. Adhesive failure at the aggregate-asphalt interface, is also predicted at locations where the aggregates geometrical edges cause stress concentrations.