Transformer defects can be identified by the FRA (frequency response analysis) that is a promising diagnostic technique. Despite the standardization in FRA measuring technique, its results interpretation is yet a research area. Because different faults types can be identified in various frequency bounds of the FRA signatures, it is necessary to identify the possible relationships between specific failures and frequency ranges in this contribution. For this purpose, a real transformer is used to conduct the essential tests, which include both healthy and faulted circumstances (axial displacement (AD), radial deformation (RD), and short-circuits (SC)). To identify efficient characteristics from the produced frequency response traces and improve interpretation accuracy of such traces, a new hyperbolic fuzzy cross entropy (FCE) measure is demonstrated and then utilized for the aim of discrimination and classification of transformer winding defects in pre-defined frequency ranges. After normalizing FRA results of the transformer under healthy and various fault circumstances the lower bounds from such responses have been extracted and then utilized to construct the desired form of the fuzzy sets of healthy and faulted circumstances. Then, a new hyperbolic FCE measure-based discrimination and classification of winding faults methodology is offered on the basis of highest and lowest FCE measure values. The highest FCE measure value between the fuzzy sets of healthy and faulted circumstances such as AD, RD and SC is designated to confirm the occurrence of winding faults in a suitable frequency range. The suggested methodology ensures smart interpretation of FRA signature and accurate classification of winding faults as it can effectively discriminate both healthy and faulted circumstances in the desired frequency ranges. The proposed approaches' performance is tested and compared by applying the experimental data after feature extraction.