Natural teeth (enamel/dentin) and most restorations are essentially layered structures. This study examines the hypothesis that coating thickness and coating/substrate mismatch are key factors in the determination of contact-induced damage in clinically relevant bilayer composites. Accordingly, we study crack patterns in two model "coating/substrate" bilayer systems conceived to simulate crown and tooth structures, at opposite extremes of elastic/plastic mismatch: porcelain on glass-infiltrated alumina ("soft/hard"); and glass-ceramic on resin composite ("hard/soft"). Hertzian contacts are used to investigate the evolution of fracture damage in the coating layers, as functions of contact load and coating thickness. The crack patterns differ radically in the two bilayer systems: In the porcelain coatings, cone cracks initiate at the coating top surface; in the glass-ceramic coatings, cone cracks again initiate at the top surface, but additional, upward-extending transverse cracks initiate at the internal coating/substrate interface, with the latter dominant. The substrate is thereby shown to have a profound influence on the damage evolution to ultimate failure in the bilayer systems. However, the cracks are highly stabilized in both systems, with wide ranges between the loads to initiate first cracking and to cause final failure, implying damage-tolerant structures. Finite element modeling is used to evaluate the tensile stresses responsible for the different crack types. The clinical relevance of these observations is considered.