In order to investigate the wind uplift resistance and failure behavior of the Continuous Welded Stainless Steel (CWSS) roof system, a combination method of static wind uplift test and numerical simulation was adopted to compare the differences in failure modes and ultimate bearing capacities of the CWSS roof system with and without sliding support imperfections. The wind uplift resistance response of the CWSS roof system was simulated using the finite element method, and further parametric studies were carried out based on the verified model. The research results show that the initial support imperfections can significantly reduce the wind uplift resistance of the CWSS roof system. When 1, 2, and 3 supports are removed, the ultimate wind pressure is reduced by 10.7%, 23.3%, and 35.7%, respectively. Reducing the width-to-thickness ratio of the roof panel has little impact on the overall ultimate bearing capacity of the roof but can enhance the flexural rigidity. Increasing the thickness of the support can notably improve the wind uplift resistance of the roof system.