A shaking table test was conducted on a negative stiffness damped outrigger (NSDO) structure, designed based on a real engineering project, to gain insights into the practical performance of the NSDO under earthquakes when equipped with nonlinear negative stiffness devices (NSD) and dampers. A low-friction NSD was designed, built, and verified by experiments to mitigate the potential issue adversely affecting its performance. The shaking table tests showed that NSD effectively increases the maximum deformation of the damper under moderate earthquakes. Nevertheless, the NSD had no influence on the initial and dynamic stiffness of the NSDO structure when the NSD was not activated due to low displacement. With the bell-shaped damping model to match modal damping ratios, a simplified fishbone numerical model was developed to simulate the response of the NSDO structure and to study the control effect of the NSDO through parametric analysis. The results revealed that the modal damping ratios were not uniform from mode to mode, and an inaccurate higher-mode damping ratio would significantly affect the response predictions during NSDO design. The initial tangential negative stiffness of the nonlinear NSD could be used to analyze the control effect under moderate earthquakes, while the secant stiffness was necessary for severe earthquakes. In addition, a combined seismic reduction curve was proposed for a two-level seismic mitigation analysis.