As has been pointed out recently, a possible solution strategy to the wear–fatigue dilemma in fretting, operating on the level of contact mechanics and profile geometries, can be the introduction of “soft” sharp edges to the contact profiles, for example, by truncating an originally smooth profile. In that regard, analysis of possible mechanical failure of a structure, due to the contact interaction, requires the knowledge of the full subsurface stress state resulting from the contact loading. In the present manuscript, a closed-form exact solution for the subsurface stress state is given for the frictional contact of elastically similar truncated cylinders or wedges, within the framework of the half-plane approximation and a local-global Amontons–Coulomb friction law. Moreover, a fast and robust semi-analytical method, based on the appropriate superposition of solutions for parabolic contact, is proposed for the determination of the subsurface stress fields in frictional plane contacts with more complex profile geometries, and compared with the exact solution. Based on the analytical solution, periodic tangential loading of a truncated cylinder is considered in detail, and important scalar characteristics of the stress state, like the von-Mises equivalent stress, maximum shear stress, and the largest principal stress, are determined. Positive (i.e., tensile) principal stresses only exist in the vicinity of the contact edge, away from the pressure singularity at the edge of the profile, and away from the maxima of the von-Mises equivalent stress, or the maximum shear stress. Therefore, the fretting contact should not be prone to fatigue crack initiation.