Glass fiber reinforced polymer (GFRP), used in insulating components like insulation rods, needs to withstand both high voltage and large dynamic mechanical fatigue during operation. In this paper, the effects of tension–compression fatigue loads on the dielectric properties of GFRP under various fatigue cycles and stress levels are investigated. The results show that DC conductivity has a strong negative correlation with stiffness, while breakdown strength is showing a positive correlation. Fatigue-induced internal damage could cause continuous charge accumulation and enhanced interfacial polarization, leading to the increase of dielectric constant by 46.89% and the reduction of breakdown strength by 15.05%, when the fatigue span ratio reaches 80% under 40% stress level. Understanding the evolution of dielectric properties of GFRP under dynamic mechanical fatigue conditions is helpful for ensuring the safe and stable operation of electrical power equipment subjected to both high voltage and fatigue loads.