Experience shows that dilution of lubricating oil with diesel oil is unfavorable to the engine, causing issues including deterioration of engine performance, shortening of oil life, and reduction in engine reliability and safety. This paper presents the verification of the hypothesis that the changes in lubricity, friction coefficient, and decreasing oil film thickness (using a relative approach, given as a percentage) are similar for lubricating oil and diesel mixtures prepared from fresh lubricating oil and used lubricating oil. To validate this hypothesis, an experiment is conducted using a high-frequency reciprocating rig (HFFR), in which the lubricity is determined by the corrected average wear scar WS1.4, the coefficient of friction μ, and the percentage relative decrease in oil film thickness r. A qualitative visual assessment of the wear scars on the test specimens is also performed after the HFFR tests. The testing covers mixtures of SAE 30 grade Marinol CB-30 RG1230 lubricating oil with Orlen Efecta Diesel Biodiesel. The used lubricating oil is extracted from the circulating lubrication system of a supercharged, trunk-piston, four-stroke ZUT Zgoda Sulzer 5 BAH 22 engine installed in the laboratory of ship power plants of the Maritime University of Szczecin. Mixtures for the experiment are prepared for fresh lubricating oil with diesel oil and used lubricating oil with diesel oil. Mixtures of these lubricating oils with diesel oil are examined for diesel oil concentrations in the mixture equal to 1, 2, 5, 10, 15, and 20% m/m. The results of the experiment confirm the hypothesis, proving that, for up to 20% m/m diesel oil concentration in lubricating oil, the changes in the lubricity of used lubricating oil diluted with diesel oil can be evaluated based on reference data prepared for mixtures of diesel oil with fresh lubricating oil. The linear approximation of μ and r trends is made with a certain margin of error we estimated. The experiment also confirms the results of previous studies which state that oil aging products in small quantities contribute to improved lubricity.