The enantioseparations of 12 isoxazoline racemates were explored with four perphenylcarbamate cyclodextrin (CD) clicked chiral stationary phases (CSPs) in high performance liquid chromatography (HPLC). The results demonstrated that the functionalities on phenylcarbamate moiety greatly determined the chiral separation ability of CD clicked CSPs. Among of them, per(3-chloro-4-methylphenylcarbamate) CD clicked CSP (CCC3M4-CSP) exhibited the best enantioseparation ability, affording 4ClPh-OPr with a chiral resolution over 20 in ternary eluent mobile phases. The optimization of CSPs structures provided wide platform for their chiral separations towards multi-mode HPLC.