Transportation corridors such as roadways are often subjected to both natural instability and cut-slope failures, with substantial physical damage to the road infrastructure and threats to the circulating vehicles and passengers. In the early 2000s, the Gipuzkoa Provincial Council of the Basque Country in Spain noted the need for assessing the risk related to the geotechnical hazards of its road network, in order to assess and monitor their safety for road users. The quantitative risk assessment (QRA) was selected as a tool for comparing the risk of different hazards on an objective basis. Few examples of multi-hazard risk assessment along transportation corridors exist. The methodology presented here consists of the calculation of risk, in terms of probability of failure and its respective consequences, and it was applied to 84 selected points of risk (PoR) over the entire road network managed by the Gipuzkoa Provincial Council. The types of encountered slope instabilities that are examined are rockfalls, retaining-wall failures, and slow-moving landslides. The proposed methodology includes the calculation of the probability of failure for each hazard based on an extensive collection of field data, and its association with the expected consequences. Instrumentation data from load cells and inclinometers were used for the anchored walls and the slow-moving landslides, respectively. The expected road damage was assessed for each hazard level in terms of a fixed unit cost (UC). The results indicate that the risk can be comparable for the different hazards. A total of 21% of the PoR in the study area were found to be of very high risk.