This article develops a probabilistic approach for assessing transport network vulnerability. A novel performance measure is proposed to evaluate the expected impact when multiple transport network components fail simultaneously at various degrees. The proposed measure captures both the likelihood and consequence of a combination of transport network component failures. The most critical combination of transport network component failures is obtained by solving a bi-level optimization problem. The upper-level problem is to solve for the combination of transport network components together with their corresponding disruption levels, which induces the maximum reduction in the performance measure. The lower-level problem is to capture the response of travelers to network changes due to network component failures and is formulated as a traffic assignment problem. The clonal selection algorithm (CSA), a biologically inspired approach, is adopted to tackle the proposed bi-level optimization problem. Numerical results indicate that neglecting partial capacity degradation and its probability of occurrence could misestimate the worst scenario, and different vulnerability assessment approaches could identify similar critical components but our approach can discover some components that are not found by other existing approaches. Moreover, it is shown that the CSA outperforms the well-known genetic algorithm in terms of solution quality in a large network.