This contribution presents an improved two-dimensional numerical model of the dynamic roller-granular subsoil interaction system that facilitates the numerical prediction of both the achieved soil compaction (“improvement depth”) and the dynamic drum response in terms of acceleration (“measurement depth”) of a specific oscillation roller. In this plane-strain model, the intergranular strain enhanced hypoplastic constitutive model captures the nonlinear inelastic behavior of the soil below the drum. The numerical simulations are performed with the Finite Element software suite ABAQUS/Standard by implementing the hypoplastic soil model using an in-house Fortran code (UMAT). Thus, the linear elastic layer applied to the soil surface (“protective foil”) proposed by the author in the original model is no longer required to ensure the numerical stability of the model. In order to study both the soil compaction and the drum response, the soil layer to be compacted is modeled with linearly increasing thickness resting on a fully compacted subsoil and a loose subsoil, respectively. The effect of a roller pass at standard excitation frequency on an initially loose soil is investigated for selected roller speeds in terms of the reduction of the void ratio. The influence of the predicted soil compaction on the drum response is simultaneously analyzed in the time and frequency domain in terms of the drum center acceleration. In addition, an experimentally found Continuous Compaction Control (CCC) parameter for dynamic rollers with an oscillatory drum is evaluated. It is shown that the developed model qualitatively predicts the fundamental response characteristics of the interacting oscillation-subsoil system observed in field tests. Moreover, the numerical model is capable of predicting the depth of influence of the selected oscillation roller.