In the Middle East, wall-like reinforced concrete (RC) columns are a common choice in multistory buildings. Sometimes, these columns need axial retrofitting for increased load capacity. In practice, unstrengthened columns bear their load, and if retrofitting is necessary, the load is released before the upgrade—unlike in past research studies that overlooked this real-world scenario. This study aimed to investigate the response of preloaded wall-like RC columns after being retrofitted using different configurations. In the experimental campaign, two half-scale columns were cast and axially loaded to 80% of their capacity, and the load was then totally released. After that, these specimens were strengthened with two different schemes, and hence, they were concentrically loaded until failure. In both schemes, the section shape was not modified. The first scheme comprised wrapping carbon FRP (fiber-reinforced polymer) sheets together with near-surface mounted (NSM) steel rebars. However, the second technique was composed of wrapping glass FRP (GFRP) sheets together with NSM steel rebars and bolted steel plates. The second scheme was found to be superior to the first one due to the extra confinement provided by the bolted steel plates. This scheme improved the peak load, stiffness, and dissipated energy by 115%, 75%, and 524%, respectively. Other than the testing campaign, nonlinear numerical modeling was undertaken to examine the behavior of tested specimens. The models were utilized to conduct a parametric study, exploring the influence of the percentage of preloading and the amount of load release on the response of columns strengthened with the second scheme.