This paper reports the temperature-dependence of methanol generation and the tensile index under ageing conditions for two paper/oil systems: one consisting of a standard wood Kraft paper and the other of a thermally-upgraded Kraft paper (TUK). A linear correlation between methanol and the tensile index for these paper/oil systems was observed in a previous study at 170 °C. In the current study, the correlation was extended to a large range of temperatures (150–190 °C). The experimental data were fitted with a modified Calvini’s kinetic model, while the Arrhenius equation was used to model the kinetic of changes of the paper’s mechanical properties during ageing. Good agreement with the temperature (lnk vs. 1/T) was observed for the rate constants of the chain-end group production, methanol formation, and the decrease of mechanical properties. The Arrhenius equation applied to this data grouping showed activation energy of 130 ± 29 kJ/mol for the decrease in mechanical strength of the standard Kraft paper, while the value was 118 ± 55 kJ/mol for the TUK paper. These values are of the same order of magnitude as those obtained in this study and in the literature for the depolymerization of cellulose and the generation of methanol that was reported. This confirmed the close relationship between cellulose depolymerization, methanol generation and the reduction of the paper’s mechanical strength during ageing, dominated by the acid hydrolysis mechanism. The results, which can be seen as a benchmark and pave the way to further research, provide an opportunity for applying the proposed correlations to estimate the insulation condition in operating transformers.