This paper analyzes the effect of sliding speed on the electrical conductivity and friction properties of the contact pair of an on-load tap changer (OLTC). Reciprocating current-carrying tribological tests were carried out on a rod–plate–copper–tin–copper contact galvanic couple at different sliding speeds in air and insulating oil media. The results show that as the sliding speed increases from 24 mm/s to 119 mm/s, the average contact resistance in air increases from 0.2 Ω to 0.276 Ω, and the average contact resistance in insulating oil also increases from 0.2 Ω to 0.267 Ω. At 119 mm/s, the maximum contact resistance in insulating oil reaches 0.3 Ω. The micro-topography images obtained by scanning electron microscopy show that with the increase in sliding speed, the wear mechanisms in the air are mainly abrasive wear and adhesive wear, and the wear mechanisms in oil are mainly layered wear and erosion craters; high sliding speed and arcing promote contact surface fatigue and crack generation. X-ray photoelectron spectroscopy was used to analyze the surface. The copper oxide in the air and the cuprous sulfide in the insulating oil cause the surface film resistance, and the total contact resistance increases accordingly. In addition, the test shows that 119 mm/s in air and 95 mm/s in insulating oil are the speed thresholds. Below these speed thresholds, the increase in contact resistance is mainly caused by mechanical wear. Above these thresholds, the increase in contact resistance is mainly caused by arc erosion and chemical oxidation processes. Non-mechanical factors exacerbate the deterioration of the contact surface and become the main factor for the increase in contact resistance.