Monitoring Shanghai metro tunnels and their surroundings indicates that the maximum settlement caused by metro operation for years has been more than 25 cm in soft soil of tunnel bottom, which has seriously affected the normal operation of subway, and even caused some old house cracking around subway lines. To investigate main influence factors on metro-caused settlement so as to provide the basis for the control of metro-caused settlement, the analytical hierarchy process was adopted to make their weight arrangement. With the experience analogy and grey correlation theory, the grey correlation-hierarchical analysis method was proposed to evaluate the possibility of metro-caused settlement in soft soil of tunnel bottom. The correlation of metro-caused settlement and its influence factors (such as dynamic load conditions of metro, soil conditions, burial conditions of soil prone to dynamic settlement, and hydrogeology conditions) was probed. Taking Shanghai Yangtze River Tunnel project in China (it is now the largest shield tunnel in the world) as an example, the division estimation and the comprehensive evaluation of possibility and severity for metro-caused settlement were also done. The results were observed as follows: (1) the severity of settlements caused by dynamic load of metro in soft soil of tunnel bottom at the same position increases as the speed of subway trains increases; (2) On comparison between the foundations of silty clay and clayey silt, the former is generally more prone to the metro-caused settlement under the same conditions as dynamic load conditions of metro, void ratio of soil, natural water content of soil, burial conditions, and hydrogeology conditions; (3) the grey correlation-hierarchical analysis method is more applicable than grey correlation method for the possibility estimation of metro-caused settlement in the soft soil of tunnel bottom; (4) it may provide the reference for the possibility evaluation of metro-caused settlement in other similar projects.