In the construction and operation stage of urban shield tunnels, joint leakage of shield is always an urgent problem to be solved. In order to further explore the waterproof performance of elastic rubber gaskets at segment joints, the finite element software ABAQUS (2022) was used to establish a fluid-solid coupling calculation model. The dynamic simulation of the leakage process at the segment joints under water pressure revealed the whole process of leakage at the segment joints and the instant water pressure value when the waterproof system failed. The results show that during the whole process from segment assembly to joint leakage, the elastic rubber gasket has experienced four key stages: gasket compression, confined water pushing, water wedge and final leakage. When the opening amount of the gasket is 6 mm and 10 mm, the contact stress between the gasket shows a “W” symmetrical distribution of high at both ends and low in the middle, and the peak of the contact stress at both ends of the interface is about twice as much as that in the middle. The waterproof threshold of the gasket is closely related to the opening amount of the gasket, and the waterproof threshold has the same trend with the initial contact stress between the gaskets.