A major problem in lubricated piston ring/cylinder liner contact sliding systems is the tribological failure mechanisms known as scuffing. In order to evaluate and better understand this damage phenomenon in these tribological systems, a tilted linear tribometer (TE77) for application-oriented reciprocating model tests was developed and validated with scuffed field engine parts. With precise oil lubrication, original engine parts, such as CKS-coated piston rings (chromium-based coating with included aluminum oxides), original liners and fully formulated lubrications, were tested under conditions similar to the most critical part of the internal combustion engines (ICEs), known as fired top dead center (FTDC). Various in situ measurements during the tests allowed for a detailed investigation of the damage processes (crack transformation) on the tribological components. For the coated piston ring, vertical cracks were attributed to residual stresses, while horizontal cracks resulted from shear stresses. The crack transformation and wear results from other studies were confirmed for the liner. The results from FIB (Focused Ion Beam) cuts, along with EDS and SEM analyses, revealed that Fe (deriving from material transfer) acts as a catalyst on the CKS layer for the tribopads and that zinc sulfides are not present everywhere.