This work investigates the influence of altered engine oil on the tribological performance, focusing in particular on wear and interconnected tribofilm formation. For this purpose, Zinc dialkyldithiophosphate (ZDDP) additivated engine oils of different degradation levels, produced in an artificial oil alteration process, were used in tribometer tests with a nitride steel piston ring against a grey cast iron cylinder liner model contact. Parameters were chosen to simulate the boundary and mixed lubrication regime typical for the top dead centre conditions of an internal combustion engine of a passenger car. Wear of the cylinder liner specimens was continuously monitored during the tribometer tests by the radio-isotope concentration (RIC) method, and tribofilms were posteriorly investigated by X-ray photoelectron spectroscopy (XPS). The results clearly show that the steady-state wear rates for experiments with altered lubricants were significantly lower than for the experiments with fresh lubricants. XPS analysis on the formed tribofilms revealed a decrease in sulphide and an increase in sulphate states for altered oils evaluated at 120 °C oil temperature, correlating with a decrease in steady-state wear rate. This finding emphasizes the role of sulphate species in the tribofilm formation process and its anti-wear capabilities, in contrast to the sulphide species and the (poly-)phosphate species, as outlined in most of the ZDDP literature. Moreover, the RIC signal that represents the amount of wear in the engine oil showed a decrease over time for specific altered lubricants and test conditions. These “negative” trends in the wear signal are remarkable and have been identified as an incorporation of wear particles from the lubricant into the tribofilm. This finding is supported by XPS results that detected an iron-oxide layer with a remarkably similar quantity within the tribofilm on the surface. Based on these findings, an assessment of the minimum film formation rate and particle incorporation rate was achieved, which is an important basis for adequate tribofilm formation and wear models.