In this paper, a novel method based on image processing is proposed for detecting the presence and location of mechanical deformations on an actual power transformer winding. A vertical imaging setup is used to obtain a two-dimensional (2-D) image of the transformer winding using synthetic aperture radar (SAR) imaging method and Kirchhoff migration algorithm. The main goal of the image processing method is to detect the location of the radial deformation on the transformer high-voltage (HV) winding. Two different deformations are applied on the winding under the test in this paper. The first one is a modeled bulgy mechanical deformation and the second one is an actual concave buckling made on the actual transformer HV winding. The experimental results for different cases show the effectiveness of the proposed method to detect the presence and location of the deformation on the transformer winding.