The mixed-mode loading fretting fatigue caused by the complex geometry of components and combinations of boundary conditions is a common failure mechanism in engineering components, which can dramatically reduce fatigue life. In this paper, a cylinder-on-flat numerical model was established to investigate tension–bending mixed-mode fretting fatigue. The finite element method in conjunction with two criteria, plane parameters McDiarmid (MD) and Smith–Watson–Topper (SWT), were used to evaluate the effects of mode angle, oblique loading, and stiffness ratio on the contact width, the maximum equivalent stress of the specimen, the surface stress, the fretting damage initiation location, and the extent of the damage initiation. The results indicate that the extent of fretting damage increases with the mode angle, and the characterization parameters are sensitive to smaller mode angles. The contact width, peak surface stress, maximum damage parameters, and damage initiation location can be effectively adjusted by the stiffness ratio. The findings may provide insights into fretting fatigue behavior under complex loading conditions, potentially contributing to enhanced structural safety and reliability for tension–bending mixed-mode loading.