Maintenance and repairing in actual engineering for long-term used structures, such as pipelines and bridges, make structural damage detection indispensable, as an unanticipated damage may give rise to a disaster, leading to huge economic loss. A new approach for detecting structural damage using transmissibility together with hierarchical clustering and similarity analysis is proposed in this study. Transmissibility is derived from the structural dynamic responses characterizing the structural state. First, for damage detection analysis, hierarchical clustering analysis is adopted to discriminate the damaged scenarios from an unsupervised perspective, taking transmissibility as feature for discriminating damaged patterns from undamaged ones. This is unlike directly predicting the structural damage from the indicators manifestation, as sometimes this can be vague due to the small difference between damaged scenarios and the intact baseline. For comparison reasons, cosine similarity measure and distance measure are also adopted to draw out sensitive indicators, and correspondingly, these indicators will manifest in recognizing damaged patterns from the intact baseline. Finally, for verification purposes, simulated results on a 10-floor structure and experimental tests on a free-free beam are undertaken to check the suitability of the raised approach. The results of both studies are indicative of a good performance in detecting damage that might suggest potential application in actual engineering real life.