This study discusses a quantitative fatigue evaluation of polymer–ceramic composites for dental restorations, i.e., commercial material (Filtek Z550) and experimental materials Ex-nano (G), Ex-flow (G). Their evaluation is based on the following descriptors: microhardness, scratch resistance, and sliding wear. In order to reflect factors of environmental degradation conditions, thermal fatigue was simulated with a special computer-controlled device performing algorithms of thermocycling. Specimens intended for the surface strength and wear tests underwent 104 hydrothermal fatigue cycles. Thermocycling was preceded by aging, which meant immersing the specimens in artificial saliva at 37 °C for 30 days. Microhardness tests were performed with the Vickers hardness test method. The scratch test was done with a Rockwell diamond cone indenter. Sliding ball-on-disc friction tests were performed against an alumina ball in the presence of artificial saliva. A direct positive correlation was found between thermocycling fatigue and microhardness. The dominant mechanism of the wear of the experimental composites after thermocycling is the removal of fragments of the materials in the form of flakes from the friction surface (spalling). Hydrothermal fatigue is synergistic with mechanical fatigue.