A new methodology is proposed to evaluate the rolling contact fatigue (RCF) performance of bearing steels in presence of surface dents. The experimental procedure consists of denting the raceway of test specimens with a hardness machine using spherical diamond tips of different radii (i.e., 200, 400, and ) and with an applied normal load ranging from . Analysis of various dent geometries yield an analytical law with five parameters useful for fitting experimental profiles for contact simulation. Fatigue tests are conducted using a two-disk machine to study the effect of different operating conditions on RCF and to compare the performances of nitrided 32CrMoV13 steel versus M50 reference steel. A numerical investigation is conducted to analyze experimental result. Initially, the local residual stresses and plastic strains around the dent are obtained through finite element simulations of the indentation process. Second, the overrolling of the dent is simulated with a contact code. Finally, an indent-based endurance limit, called H1I, is proposed and comparisons are made with test results. Both RCF tests and numerical simulations show improved performance with nitrided 32CrMoV13 steel when compared to the M50 reference steel. The dominating role of sliding is also experimentally highlighted and two areas of damage initiation are identified. The effects of normal load and hoop stress are less marked.