We report numerical simulation results based on rigorous analytic solutions of scalar wave scattering caused by a cylinder buried in a planar substrate. As there are multiple interactions between the planar substrate and the cylinder, theoretical solutions were expressed in the form of coupled sets of infinite series, with each term within the series explicitly reflecting the effect of multiple scattering of increasing order. We determined the near- and far-field distributions of (1) the reflected field in the air, (2) the scattered and transmitted fields in the substrate, and (3) the transmitted field within the cylinder. Our results indicate that the effects of higher-order multiple scattering depend on the size, location, and refractive index of the cylinder, especially in the near-field region. The simulation is generalizable, as it places no restrictions on the physical and geometrical qualities of the cylinder or the planar substrate.