To investigate the stereo coordination effect on the optical resolution, chiral monomer (+)-5-oxobornyl methacrylate (OBMA) was synthesized and then polymerized under various conditions. In this work, optical resolution was carried out in the presence of chiral polymers having (+)-5-oxobornyl moieties as chiral stationary phase (CSP) for high-performance liquid chromatography (HPLC). Chiral polymer was immobilized on the surface of hydrophobic silica gel, and the chiral recognition ability of the chiral polymers was investigated. Effects of operation temperature and eluent flow rate on the chromatographic resolutions were investigated. The results of optical resolution were compared with those observed in our previous paper using chiral polymers (CSP-1 and CSP-2) having 2,3-dihydroxybornyl moieties as chiral stationary phases. It was found that the recognition ability of poly(OBMA) is greater than those of CSP-1 and CSP-2.