This paper presents a computational study on a new method of detecting multiple simultaneous damages in a cable-stayed bridge by use of the analysis of the vertical dynamic response of a vehicle passing the bridge. First, the study uses a finite-element method to simulate the vehicle cable-stayed bridge system. Then, the vertical vibration interaction between the bridge and the vehicle is solved by a time-step integration scheme. In this research, we consider that two kinds of damage including cable tension loss and deck damage may occur simultaneously at different locations. The differences between the vertical displacement responses of a vehicle passing the damaged bridge and the healthy bridge are sampled and called the relative displacement response vector of the vehicle. The proper orthogonal decomposition (POD) is utilized to decompose the relative displacement response vector of the vehicle passing the bridge with unknown multiple damages into an optimal set of basis vectors formed from the ones of the vehicle moving over the known damaged bridges. The associated system parameters variation with the unknown multiple damages can be reconstructed further. Discussions are given concerning the feasibility and limitation of the proposed detection technique as well as directions for future research.