SUMICHIRAL^® is the trade name for chiral stationary phases of Samika Chemical Analysis Service, Ltd. and began as GC chiral stationary phases in the 1970s. In the 1980s, the focus of research and development shifted from GC to HPLC, and chiral stationary phases using low molecular weight chiral selectors, such as Pirkle type and ligand exchange type, were developed. Among them, SUMICHIRAL^® OA-2000 is the prototype of the Pirkle type chiral stationary phase and is used for isomer separation of pyrethroid insecticides. In addition, SUMICHIRAL^® OA-5000, which is a ligand exchange type is an extremely versatile chiral stationary phase that can directly perform chiral separation of many amino acids and lactic acid without derivatization. From the 1990s to the 2000s, we developed and commercialize the host-guest type chiral stationary phases, such as SUMICHIRAL^® OA-7000 using β-cyclodextrin derivatives and SUMICHIRAL^® OA-8000 using chiral pseudo-18-crown-6-ether derivative. Furthermore, SUMICHIRAL^® OA-7700, acetylating β-cyclodextrin type, was shown to have excellent enantioselectivity for many aromatic chiral amines. We performed theoretical considerations on the separation mechanism of chiral stationary phases, and based on these findings, we proposed a method for selecting a chiral stationary phase that depends on the functional groups of the chiral analytes. Many chiral stationary phases developed have been commercialized, and are expected to be effectively utilized for chiral separation analysis of pharmaceuticals, physiologically active substances, etc.