In this chapter, a simulation chain is described and applied to an asphalt test track and a highway pavement structure. The simulation chain consists of different modules reaching from the experimental identification of the asphalt material, its numerical modeling on the material scale via adequate models to finally the structural scale of the pavement and the vehicle-tire system, which is numerically assessed in the framework of a coupled vehicle-tire-pavement system. Relative dynamic effects of vehicle-tire-pavement interaction have been investigated based on a multibody analysis of the vehicle driving on a rough pavement surface (external stimulus). For the pavement simulation, equivalent tire loads are used in an arbitrary Lagrangian Eulerian framework for tire and pavement. Finally, the rut formation is computed by varying different influence factors (climate temperature, vertical tire force, type of asphalt material of the surface layers etc.). With the help of the simulated deformed pavement geometry (whole service life), surface drainage characteristics are finally analyzed and assessed via a surface drainage module, e.g. to compute and predict the alteration of the pavement runoff during the service life of the pavement.