Managing a large fleet of ageing assets has become a technical challenge faced by many electricity utilities in developed countries. Asset managers are increasingly interested in techniques that can help extend the useful lifetime of a transformer. Oil regeneration is one of such techniques. In this paper, oil regeneration experiments were performed on a 6.4/0.4 kV retired distribution transformer to investigate the effect of oil regeneration on improving paper conditions. Oil regeneration was conducted in two stages, with the first stage aimed at ‘cleaning the oil’ and the second stage targeted at ‘cleaning the paper’. Oil samples were collected at regular intervals throughout the process and paper samples were obtained from the transformer before and after each oil regeneration stage. It was found that oil regeneration restores oil parameters, including moisture and acidity, similar to those of new oils at the end of stage 1. Analysis of paper samples indicated a reduction in paper moisture at the end of stage 2 by nearly 40%, while low molecular weight acids (LMA) in paper exhibited a reduction by around 30% on average. It is found that the extended oil regeneration period, i.e., stage 2, is necessary to improve the paper condition and hence to reduce the paper ageing rate.