Groundwater leakage in shield tunnels poses a threat to the safety and durability of tunnel structures. Disturbance of adjacent constructions during the operation of shield tunnels frequently occurs in China, leading to deformation of tunnel lining and leakage in joints. Understanding the impact of adjacent constructions on the waterproofing performance of the lining is critical for the protection of shield tunnels. In this study, the weakening behavior of waterproof performance was investigated in the joints of shield tunnels under transverse deformation induced by adjacent construction. First, the relationship between the joint opening and transverse deformation under three typical adjacent constructions (upper loading, upper excavation, and side excavation) was investigated via elaborate numerical simulations. Subsequently, the evolution of the waterproof performance of a common gasket with a joint opening was examined by establishing a coupled Eulerian–Lagrangian model of joint seepage, and a formula describing the relationship between waterproof performance and joint opening was proposed. Finally, the weakening law of waterproofing performance was investigated based on the results of the aforementioned studies. It was determined that the joints with the greatest decline in waterproof performance were located at the tunnel shoulder in the upper loading case, tunnel crown in the upper excavation case, and tunnel shoulder in the side excavation case. When the waterproof performance of these joints decreased to 50% and 30%, the transverse deformations were 60 and 90 mm under upper loading, 90 and 140 mm under upper excavation, and 45 and 70 mm under side excavation, respectively. The results provide a straightforward reference for setting a controlled deformation standard considering the waterproof performance.