Ideally, rolling bearings would always be operated in controlled clean environments and with perfect mounting conditions. However, in many cases, contamination as well as impact damage during mounting occurs. This can result in damage to the bearing raceways due to overrolling of particulate matter or uncontrolled contact of mating surfaces. The influence of such surface deformations on the bearing fatigue life has long been and still is a topic of research for bearing suppliers as well as for customers. In this work, the effect has been studied by a stringent simulation approach starting from the initial material deformation mechanisms to fatigue simulation and subsequent rating life analysis. Two-dimensional as well as three-dimensional deformation simulations were applied to identify the stress and strain formation during initial indentation and subsequent overrolling of damage features in the raceway of bearing rings. The evolution of stress and strain states were simulated for multiple overrolling events until saturation occurred. Subsequently, the resulting stress fields were analyzed in a local-stress-based rating life model. Several shapes and sizes of predamage were modeled, and the effect on the calculated lifetime was compared. This simulative approach was accompanied by experimental validation on artificially predamaged bearing raceways to compare calculated rating life with experimental test life data. It can be shown that the size, shape, and curvature of the damages are not necessarily dominant factors for the effect of indentations on bearing life. The most dominant factor proves to be the size of the material ridge formed due to the material flow at the indent. For the testing conditions and size of the tested bearings, a threshold for the life-limiting ridge heights could be derived from simulations, which was found to be in good agreement with results from the life tests.