The leakage evaluation when gas is used is more severe than that when liquid is used in pipe flange connections. In a practical design, it is also necessary to examine the leakage in the connections under liquid internal pressure application. The contact gasket stress distribution in the connection with a spiral wound gasket subjected to internal pressure and bending moments were analyzed using elasto-plastic (EP) finite element method (FEM) taking account hysteresis and nonlinearity in the stress-strain curve of the gasket. The effects of initial clamping bolt force (bolt preload), the nominal pressure and the nominal diameter of pipe flange and the equivalent pressure when the leakage occurs on the contact gasket stress distributions were examined. The leakage tests for the connections under the bending moments and the internal pressure were also conducted by using liquid (water). By using the results of the leakage tests and the calculated contact gasket stress distributions, the sealing performance of the connections was evaluated. It was found that the sealing performance of the connection can be estimated when liquid (water) was used, that is, when the contact gasket stress becomes zero, the leakage occurs. In addition, a method for determining the bolt preload in the connections under the bending moments was proposed for the reliable design.