The corrosive sulfur compounds present in the mineral oil causes the formation of dibenzyl disulfide (DBDS) complex and it can also erode the on-load tap changing selector contacts leading to generation of silver sulfide (AgS2).The present work reports the effect of DBDS and Ag2S concentrations in mineral oil on thermally aged pressboard material. The results demonstrate that surface discharge inception voltage (SDIV) is higher for the aged pressboard specimen. The higher concentrations of DBDS showed a reduction of more than 50% in the magnitude of SDIV compared to its effect with the addition of Ag2S. The surface potential analysis indicates a higher initial potential for the aged specimens with an increased half lifetime. In addition, only deep traps observed on the aged specimens with a slight right shift in its trap energy level. The mechanical strength of aged pressboard specimens with DBDS and Ag2S is understood using tensile testing and simultaneous analysis is captured using Digital Image Correlation (DIC) technique to understand its strain percentage at different areas on the pressboard material during its elongation. The laser induced breakdown spectroscopy (LIBS) analysis is performed to identify the elements responsible for thermal ageing such as carbon, copper and sulfur on the surface of pressboard material. The plasma temperature calculated from sulfur peaks is higher for DBDS aged specimen compared to AgS2 and a linear correlation is observed on the LIBS intensity with ageing duration. Further, the Principal Component Analysis (PCA) is used for its classification on the degradation of pressboard due to the diffusion of both copper and silver sulfide from the mineral oil. The two principal components (PC1 and PC2) provided a higher variance of 99.8% with a clear classification observed between the unaged and aged pressboard specimens due to the addition of both DBDS and Ag2S in mineral oil.