The implementation of Structural Health Monitoring (SHM) offers the prospect for sustainable and safe service‐life extension of existing bridges, a large portion of which is approaching the end of their nominal life. Many SHM frameworks for civil infrastructure address timely damage detection and identification. However, the scarcity of case studies on real damaged bridges hinders the generalized application of SHM in practice. In this contribution, monitoring data from a four‐day campaign on the Ponte‐Moesa bridge, a three‐span concrete box‐girder bridge, is presented as a benchmark for data‐driven damage diagnosis schemes. The monitoring data, covering accelerations from ambient and forced vibrations, contains the reference state after concluding the service life along with several gradually increasing damage states, including drilling holes and cutting reinforcement rebars and prestressed cables. The potential of damage‐sensitive features to identify damage is presented and the uncertainties, resulting from the environmental and operational conditions and sensor malfunctioning, pertaining to robust damage detection are discussed. Drawing from real bridge monitoring data, a range of prospects and open challenges of vibration‐based SHM for bridges are reviewed.