High voltage circuit breakers (HVCBs) play a critical role on providing the desired reliability, and resiliency in power systems. In order to extend their lifetime and predict the failures, various maintenance policies could be applied on these critical components. Amongst these strategies, condition-based maintenance (CBM) provides a satisfactory agreement with future smart environment. This paper aims to provide an insight into the relevant developments in this subject and to explore the viable visions compatible with future research stream. Accordingly, three directions, i.e. diagnostic signals, intelligent modelling and using monitoring data in asset management have been addressed in this paper. It presents challenges dealing with real-time assessment of the diagnostic signals relating to measurements, and analyses. Subsequently, the issues associated with using artificial intelligent (AI) and Machine learning for providing intelligent algorithms have been discussed. Finally, the connection between the monitoring data and the asset management approach is investigated. The latter is looking for the subjects including remaining lifetime estimation, prioritization, and health index definitions. This paper has attempted to make a bridge from past to future research trends in the failure diagnosis of HVCBs.