One-sided bolts are commonly used for bolted connections between closed section members to address the issue of insufficient space for nut installation. Among them, the elliptical head one-sided bolt uses the difference in length between its long and short axes. This allows the bolt head to be inserted into the elliptical bolt hole and subsequently rotated by 90 degrees, effectively achieving anchoring. But the use of elliptical bolt holes may cause some problems, such as bolt slippage and stress concentration around the bolt holes. In this paper, building upon the elliptical head one-sided bolt concept, a novel structure for one-sided bolted connection is proposed, incorporating a plug-in gasket to improve the mechanical properties of the elliptical one-sided bolted joints. Six sets of steel plate double-lapped joints, connected by elliptical head one-sided bolts and plug-in gaskets, were designed for shear resistance tests. A finite element model was designed using ABAQUS, based on the test specimen parameters. By comparing the simulation results with the experimental findings, the reinforcing effect of the gasket on joint stress was analyzed and validated. The results show that the plug-in gasket effectively resolves the excessive slippage issues and enhances the initial stiffness of the joint. Moreover, when pressure is applied to the bolt hole, the plug-in gasket reduces the stress concentration caused by the extrusion between the bolt hole and the bolt shank, thus preventing local premature failure of the bolt hole.