The objective of this study is to monitor the health status of harbor caissons which have potential foundation damage. To obtain the objective, the following approaches are performed. Firstly, a structural damage monitoring(SDM) method is designed for interlocked multiple-caisson structures. The SDM method utilizes the change in modal strain energy to monitor the foundation damage in a target caisson unit. Secondly, a finite element model of a caisson system which consists of three caisson units is established to verify the feasibility of the proposed method. In the finite element simulation, the caisson units are constrained each other by shear-key connections. The health status of the caisson system against various levels of foundation damage is monitored by measuring relative modal displacements between the adjacent caissons.