A winding condition assessment process using FRA can be treated as an MADM problem by combining subjective and quantitative evidence. In this chapter, first an FRA assessment process is introduced briefly, which is then mapped into an MADM problem under an ER framework adopted for winding condition assessment. Subsequently, several examples of transformer winding condition assessment problems are presented using two ER evaluation analysis models, where the potential of the ER approach in combining evidence and dealing with uncertainties is demonstrated. In the case when more than one expert is involved in an FRA assessment process, the developed ER framework can be used to aggregate subjective judgements and produce an overall evaluation of the condition of a transformer winding in a formalised form.