The effects of cyclic internal pressure and thermal changes on the sealing performance and mechanical behaviors in pipe flange connection are examined using the FEM analyses for pipe flange connections with spiral wound gasket (SWG). The contact gasket stress distributions and the axial bolt forces taking into account the cyclic internal pressure and thermal changes are demonstrated. The load (internal pressure, thermal changes) sequences are determined from the conditions for actual pipe flange connections used in petroleum and chemical plants. Furthermore, the effect of material differences between pipe flange and bolts on the contact gasket stress distribution are examined. From the FEM results, it is found that the contact gasket stress reduces to be the smallest when a plant is restarted. The reduced contact gasket stress should be taken into account in the sealing design of the connection. On the other hand, the leakage tests were carried out to verify the FEM results and the effect of number of cycles (for 21days). A fairy good agreement is seen between the estimated amount of leakage due to the contact gasket stress distributions obtained from the FEM and the measured amount of leakage. It is found that the contact gasket stress decreases when the plant is restarted and as the temperature decreases. At that time, the contact gasket stress is the smallest which may lead to a leakage accident.