Surface-defect-induced pitting gradually becomes the limitation of the rolling contact fatigue life of the M50 bearing steel as the subsurface initiation spalling probability decreases recently. Dent formation lives residual stress (RS). However, it was ignored in past studies on surface-initiated pitting. Therefore, this study established a continuous simulation model from particle compression to cycle rolling contact loading to study the dent-induced RS effects on damage evolution. The constitutive model of damage evolution incorporated continuum damage mechanics and cohesive mechanics. The results show that the depth-width ratio of the dent and RS increases as the load and hardness increase. RS makes both subsurface-initiation-damage and surface-initiation-damage advance, and affects the direction and speed of the surface damage evolution. Moreover, the size of the pitting in the rolling direction increases as hardness increases.