Power transformers are very vital components in electrical power network. Deterioration of transformer’s insulation has significant impacts on its health condition. Hence, detailed analysis of insulation testing attributes is very important in diagnosing the transformer. It is possible with an effective decision-making system. In the present paper, a new grey relational-based fuzzy logic expert system is proposed for continuous health monitoring of power transformers. In this approach, ranking-based qualitative relational analysis is initially carried out in order to reduce large number of input attributes into three input health grades. These input grades are further integrated with a technically designed expert fuzzy rule base. Outputs of the proposed model are validated with the outputs of multi-criterion based fuzzy logic model presented in Reference [29]. Testing data of 200 in-service transformers are utilised in the validation of both the models. It is observed from the comparison that similarity index of the proposed grey-fuzzy system is 92 percent. Several issues exist in regular transformer health assessment models such as the large number of rules, uncertainties, requirement of large training data, complexity issues are overcome by integrating the grey relational analysis with the fuzzy logic system. The proposed model can be easily implemented by all utilities and diagnostic experts of transformers.