In this paper, the dynamic behavior of one degree-of-freedom oscillator subject to stick–slip and wear phenomena at the contact interface with a rigid substrate is investigated. The motion of the oscillator, induced by a harmonic excitation, depends on the tangential contact forces, exchanged with the rigid soil, which are modeled through piecewise nonlinear constitutive laws, accounting for stick–slip phenomena due to friction as well as wear due to abrasion, already developed by the authors in a previous work. The nonlinear ordinary differential equations governing the problem are derived, whose solution is numerically obtained via a typical Runge–Kutta-based algorithm. The main target of this study is to analyze and discuss the strong nonlinear behavior, descending from the presence of stick–slip and wear phenomena, thus investigating the effect of the different interface modeling. In this framework, the analysis is carried out considering the whole evolution of non-smooth contact laws, starting from the virgin interface.