Starting from the current need for the safety of energy systems, in which power transformers play a key role, the study of the health of power transformers in service is a difficult and complex task, since the assessment consists of identifying indicators that can provide accurate data on the extent of degradation of transformer components and subcomponents, in order to establish a model for predicting the remaining life of transformers. Therefore, this paper proposes a model for assessing the remaining service life by diagnosing the condition of the transformer based on the health index (HI) obtained from a multi-parameter analysis. To determine the condition of power transformers, a number of methods are presented based on the combination of the combined Duval pentagon (PDC) method and ethylene concentration (C2H4) to determine the fault condition, the combination of the degree of polymerisation (DP) and moisture to determine the condition of the cellulose insulation and the use of the oil quality index (OQIN) to determine the condition of the oil. For each of the classification methods presented, applications based on machine learning (ML), in particular support vector machine (SVM), have been implemented for automatic classification using the Matlab development environment. The global algorithmic approach presented in this paper subscribes to the idea of event-based maintenance. Two case studies are also presented to validate SVM-based classification methods and algorithms.