The fatigue life of circular rubber bearings under cyclic compression is theoretically and numerically analyzed based on a previously proposed fatigue failure mechanism. The energy release rate at any point in circular rubber bearings under cyclic compression, which depends on the cracking energy density and crack length along the predicted crack propagation path, is derived first theoretically. Then, the corresponding fatigue crack growth rate and fatigue life are determined numerically by introducing the fatigue parameters of three different rubber compounds before and after suffering from thermal aging. Meanwhile, the effects of intrinsic flaw size and maximum compressive stress on the fatigue life of circular rubber bearings are also investigated. It is found that the enlargement in the Regime 1 range of the crack growth rate of rubber increases the fatigue resistance of circular rubber bearings. Therefore, the effects of the mechanical properties, intrinsic flaw size, threshold value, and maximum cyclic compressive stress on fatigue life are significant and should be taken into account in designing rubber bearings.