Pipe flange connections with gaskets in chemical plants, electric power plants and other industrial plants are usually exposed to elevated internal pressure with cyclic thermal condition. It is important to investigate the sealing performance of pipe connections under long term severe thermal exposure swings to ensure operational safety. In this study, the effects of cyclic thermal conditions on the sealing performance and mechanical characteristics in larger and smaller nominal diameter of pipe flange connection are examined using FEM calculations. Helium gas leakage is predicted using the contact gasket stress obtained from the FEM results. On other hand, the leakage tests using the smaller nominal diameter of pipe flange connection were conducted to measure the amount of helium gas leakage and to compare with the predicted amount of gas leakage. As the results, the contact gasket stress distributions were changed dramatically under cyclic thermal condition and elevated internal pressure. In the pipe flange connections with smaller nominal diameter, the contact gasket stress was the smallest in the restart condition. On other hand, the minimum contact gasket stress in the pipe flange connection with larger nominal diameter was depending on the materials of connection. In the pipe flange connection with larger nominal diameter, the contact gasket stress distributed and changed in the radial direction due to the flange rotation. A fairly good agreement was found between the experimental leakage result and predicted leakage results.