Adhesive bonding is increasingly being incorporated into civil engineering applications. Recently, the use of structural adhesives in steel-concrete composite systems is of particular interest. The aim of the study is an experimental investigation of the damage assessment of the connection between steel and concrete during mechanical degradation. Nine specimens consisted of a concrete cube and two adhesively bonded steel plates were examined. The inspection was based on the ultrasound monitoring during push-out tests. Ultrasonic waves were excited and registered by means of piezoelectric transducers every two seconds until the specimen failure. To determine the slip between the steel and concrete a photogrammetric method was applied. The procedure of damage evaluation is based on the monitoring of the changes in the amplitude and phase shift of signals measured during subsequent phases of degradation. To quantify discrepancies between the reference signal and other registered signals, the Sprague and Gears metric was applied. The results showed the possibilities and limitations of the proposed approach in diagnostics of adhesive connections between steel and concrete depending on the failure modes.