Surface Discharge Inception Voltage (SDIV) of unaged and copper sulphide diffused Oil Impregnated Pressboard (OIP) material was studied by adopting Ultra High Frequency (UHF) technique. Copper sulphide diffusion into OIP material was carried out by thermal aging of pressboard material in Dibenzyl Disulphide (DBDS) added transformer oil. The SDIV reduces with increase of thermal aging temperature. The current pulse injected in positive and negative half cycle during the surface discharge of the AC shows the rise time of 0.8ns and 1ns respectively. The FFT analysis of UHF signal measured during surface discharge process has shown frequency content in the range 0.7-1.2 GHz with its dominant frequency at 0.9 GHz. The life of the charge presented on the pressboard increases with thermal aged specimen. Energy dispersive spectroscopy (EDS) analysis of OIP material indicates presence of copper and sulphur content. Frequency Domain Dielectric Spectroscopy (FDDS) studies indicate the permittivity(ϵr), dissipation factor (tan(δ)), conductivity (σdc) increases and relaxation time (τ), coefficient (α) decrease with OIP material (in air / Nitrogen) aged at higher temperature in DBDS added transformer oil. Cole-Cole double relaxation model was used to understand the dielectric parameters of copper sulphide diffused OIP material. The DC conductivity of pressboard material aged in DBDS included transformer oil follows Arrhenius law and the activation energy decreases with increase in temperature of thermal aging. © 1994-2012 IEEE.