In this study, three types of silicone rubbers, namely, insulative silicone rubber, conductive silicone rubber and silicone rubber with conductive as well as insulative layers are investigated for their compatibility with mineral oil. Mineral oil with different silicone rubber samples is thermally aged at 130 °C for 360 h, 720 h and 1080 h and at 23 °C, 98 °C and 130 °C for 360 h. At the end of each ageing interval, mineral oil and oil-impregnated silicone rubbers are investigated for their dielectric properties. Aged mineral oil samples are investigated for their moisture content, breakdown voltage, colour number, dissolved gases and total acid number, whereas solid insulation samples are investigated for their moisture content. Additionally, pressboard samples in mineral oil and mineral oil without any solid insulation materials are also aged under the same conditions and are investigated for their dielectric properties. From the obtained results, it can be assessed that the presence of carbon particles in conductive silicone rubber negatively impacts the dielectric properties of mineral oil. Among the investigated silicone rubbers, the insulative silicone rubber exhibits good compatibility with mineral oil and a strong potential for being used in mineral oil.