We investigated whether low transformation temperature (LTT) welding materials are beneficial to the generation of compressive residual stress around a weld zone, thus enhancing the fatigue performance of the welded joint. An experimental and numerical study were conducted in order to analyze the residual stress in multi-pass T-welded joints using LTT welding wire. It was found that, compared to the conventional welded joint, greater tensile residual stress was induced in the flange plate of the LTT welded joints. This was attributed to the reheat temperature of the LTT weld pass during the multi-pass welding. The formerly-formed LTT weld pass with a reheat temperature lower than the austenite finish temperature converted the compressive residual stress into tensile stress. The compressive residual stress was generated in the regions with a reheat temperature higher than the austenite finish temperature, indicating that LTT welding materials are more suitable for single-pass welding.