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With the increasing use of sensors and wireless communication systems, predictive maintenance is acquiring more and more importance to assess the condition of in-service equipment. Predictive maintenance presents promising cost savings, as it allows minimizing unscheduled power systems faults, which can have very costly and catastrophic consequences. Early stage detection of power system failure requires acquiring, monitoring, and periodically analyzing the condition of the elements involved, such as high-voltage power connectors, since they are critical devices which are often located in key points of power systems. This paper proposes a low-cost online system to determine the contact resistance of high-voltage direct current (dc) and alternating current (ac) power connectors, to determine their health condition in order to apply a predictive maintenance plan. The contact resistance is considered as a reliable indicator of the connector's health condition. However, it cannot be directly measured, and the applied strategy differs between dc and ac power systems. The experimental results show a maximum uncertainty of 4.5%, thus proving the accuracy and feasibility of the approach presented in this paper, since the proposed limit of acceptable resistance increase is 20%. This approach can also be applied to many other power systems' elements.