Condition monitoring data can be used to assess the health of a power system component but is rarely used to assess the reliability of the power system they are part of. For high-voltage circuit breakers (HVCBs), the susceptibility to various failures can be assessed by examining trip coil current (TCC) measurements. HVCBs have two failure modes, failure to trip on command and tripping without a command, which are triggered by various failure mechanisms that in turn may depend on the technical condition of the HVCBs. The aim of this paper is to demonstrate a methodology for quantifying the impact that the technical condition of HVCBs has on the power system reliability indices. An equivalent transmission line failure rate considering protection system failures, including failures related to HVCBs, can be calculated by computing contributions from various fault types (FTs). This paper proposes a framework that can quantify the frequency of the FTs that are affected by HVCB condition. The system-level effects are then evaluated using approximate methods for power system reliability evaluation. To demonstrate the principles and benefits of this methodology, a case study is presented that incorporates HVCB condition data from the Icelandic transmission grid into an illustrative 4-bus test system; a dataset of 83 TCC measurements from 38 HVCBs from the Icelandic Transmission System Operator is used, together with an outage database of life histories of 464 HVCBs from the Icelandic transmission grid. Results indicate that the condition deterioration associated with the probability of an HVCB failing to trip on command can significantly degrade the reliability indices.