Chromium and silicon are often introduced to increase the performance of TiAlN hard coatings in dry tribological contacts. The addition of Cr and Si during a high-power impulse magnetron sputtering (HiPIMS) deposition process leads to high-quality TiAlCrSiN films. In this paper, the analysis of friction and wear of these films is conducted by oscillation tribometry under dry conditions with a subsequent mapping of the surface topography. Both abrasion- and adhesion-dominated conditions are realized using different steel counter bodies. Oscillation-frequency-dependent experiments show a significant impact of the compositional variation on friction and wear. It is shown that the TiAlCrSiN coating investigated has a higher coefficient of friction and a lower wear resistance compared to counterparts made of 100Cr6. The friction coefficient could be reduced by using a V2A counterpart. The results can be understood in terms of a reduced adhesion of both oxidic and metallic wear debris at the TiAlCrSiN surface. The study provides valuable progress towards the development of advanced cutting tools, e.g., for stainless steel.