Controlled rocking systems have been used in numerous structures around the world as a seismic force resisting system. In a controlled rocking wall system, the wall is allowed to uplift from the foundation during seismic events, thus reducing its lateral stiffness and minimizing the corresponding seismic force demands. This rocking response is controlled using a combination of post-tensioning and supplemental energy dissipation. In this way, controlled rocking walls are designed to have less damage than conventional systems and to have also near-zero residual deformations. Promising strides have been taken to apply the concept of controlled rocking systems to masonry walls; however, several issues have been encountered due to the low strength and brittle nature of the masonry material in compression during rocking. In addition, there are many challenges with the numerical modeling of such masonry walls due to the variability of the material itself and the anisotropic nature of the systems they form. The current paper develops and validates a numerical model to capture the performance of a confinement system for the rocking point at the wall toe, a key region of a controlled rocking masonry wall (CRMW). While maintaining the footprint of the wall, this system provides enough space for replaceable energy dissipation devices to be installed in order to address the low inherent damping in CRMWs. In the current study, the developed model represents the concrete masonry units, grout and reinforcement with multi-layer shell elements available in OpenSees. To validate the model, compression tests for several grouted masonry assemblages, some of which adopt such a confinement system, are used. These assemblages were recently tested as a part of a multi-phase research program that was initiated at McMaster University to advance the use of CRMWs as a seismic force resisting system in lieu of conventional masonry shear walls. The validation results show how numerical models can capture and assess the performance of the confinement system, with the end goal of enhancing the seismic performance of CRMWs.