In a pavement management system (PMS), time to maintenance is generally estimated based on the predicted condition of the pavement. Usually a deterministic approach is applied in the PMS to estimate the time to maintenance by following the deterioration equation of the performance index. However, it is necessary to be aware of the probability of failure to investigate whether the estimated time to maintenance by the deterministic approach is reasonably probable. For this reason, a probabilistic approach is applied in this study to estimate the probability of failure over the estimated time to maintenance. In this approach, the probability of failure is estimated from the distribution of the mean time to maintenance by considering both the overall condition of the pavement and individual instances of distress. These mean times to failure or maintenance are calculated from the overall condition of pavement in relation to the pavement condition index (PCI) when the trigger value becomes 65 or less. A pavement may be expected to fail, however, because of any specific distress before it reaches the PCI trigger value for maintenance. For this reason, the probability of failure of each specific distress is also investigated by using a Monte Carlo simulation. It is found that the survival probability up to the fifth year is approximately 80% to 90% for each category of traffic and material type based on the overall condition, and the probability of failure for individual distress is very low over the performance cycle.