The literature on the subject and the results of numerous research experiments indicate that single replacement cycles do not reflect the actual state of oil quality in the context of its degradation. Monitoring the operational quality of the oil in several successive stages allows for a more accurate diagnosis of the optimal oil change time. Therefore, it was decided to investigate the relationship between two consecutive periods of changing the operating oil in an engine. Comparative tests of seven buses included in the fleet were carried out. An important division criterion was taken into account—the operation of city and intercity buses. The HDXRF instrumental chemical analysis method was used to determine changes in the content of abrasive metals, and additives in engine oils. Additionally, the oxidation, nitration, sulfonation, and soot content were assessed using infrared spectroscopy (FTIR) based on the ASTM E2414-10 standard and kinematic viscosity at 40 °C and 100 °C using a Stabinger viscometer according to ASTM D7042. The course of these changes was analyzed in terms of their dynamics. The comparative study aimed to identify trends and sources of differences between the tested oils, as well as to demonstrate the number of exceedances of limit values for the selected parameters.