Rubber surfaces exposed to concentrated, sliding impacts carry large normal and shearing stresses that can cause damage and the eventual removal of material from the surface. Understanding this cut-and-chip (CC) effect in rubber is key to developing improved tread compounds for tires used in off-road or poor road conditions. To better understand the mechanics involved in the CC process, an analysis was performed of an experiment conducted on a recently introduced device, the Coesfeld Instrumented Chip and Cut Analyser (ICCA), which repetitively impacts a rigid indenter against a rotating solid rubber wheel. The impact process is carefully controlled and measured on this lab instrument, so that the contact time, normal force, and shear force are all known. The numerical evaluation includes Abaqus finite element analysis (FEA) to determine the stress and strain fields during impact. The FEA results are combined with rubber fracture mechanics characteristics of the material as inputs to the Endurica CL elastomer fatigue solver, which employs critical plane analysis to determine the fatigue response of the specimen surface. The modeling inputs are experimentally determined hyperelastic stress-strain parameters, crack growth rate laws, and crack precursor sizes for carbon black–filled compounds wherein the type of elastomer is varied in order to compare natural rubber (NR), butadiene rubber (BR), and styrene-butadiene rubber (SBR). At the lower impact force, the simulation results were consistent with the relative CC resistances of NR, BR, and SBR measured using the ICCA, which followed the order BR > NR > SBR. Impact-induced temperature increases need to be considered in the fatigue analysis of the higher impact force to provide lifetime predictions that match the experimental CC resistance ranking of NR > SBR > BR.