The large power transformer is one of the most expensive assets in a power system network.Special attention needs to be taken to monitor this expensive asset. Among the most critical aspect of a transformer that needs to be monitored is the mechanical condition of the windings and core.One of the best approaches to achieve this is by performing the Frequency Response Analysis (FRA) test on the transformer. The test measures the transfer function response of the transformer winding. If any physical changes occur, it will affect the original response, which can be used to detect any abnormality. However, the critical challenge in this technique is to correctly interpret the measured response in determining the transformer status. Although various investigations have focussed on this issue, the interpretation aspect of FRA is still not fully established.In order to contribute to the improvement of a FRA interpretation scheme, this thesis investigates the sensitivity of FRA measurement on several common winding deformations and explores a new potential diagnostic scheme of FRA. A wide range of power transformers have been used throughout this study ranging from a small sized prototype laboratory transformer to a 30 MVA power transformer installed at a substation.Initially, a mathematical model is established to simulate the frequency response of a power transformer. This is achieved by comparing three models, which are available in the literature.These models are compared in terms of their accuracies to simulate the response and their applicability to studying winding deformation. The comparison shows that the multi-conductor transmission line model is the best approach due to its ability to model each turn of a winding.With the developed model, the sensitivity of the winding response is investigated. This study shows that a minor change to the winding geometrical parameters could cause a considerable change on the response. On a different issue, it is found that a similar winding failure mode may cause a different response variation depending on the winding type. A study based on measurement is also conducted to investigate the influence of windings from other phases to the tested winding. It reveals that the end to end open circuit response is susceptible to the condition of an adjacent winding. Additionally, investigation on the winding response sensitivity due to the tap changer setting is also carried out.This thesis studies several winding deformations, which includes tilting and bending of conductors and inter-disc fault. These three faults are examined in terms of their severity of damage and location of the fault. Statistical analysis is applied to determine the overall condition of the winding. On the other hand, transfer function based analysis is proposed to extract further iii information if the winding is found to be faulty. This includes using the pole plot and Nyquist plot, in which the latter proved to be useful for all winding failure modes. The transfer function is achieved by applying vec...