Two cyclodextrin-based chiral stationary phases have been prepared by immobilization of functionalized mono-6-azido- -CD derivatives to alkynyl modified silica via "click" chemistry and applied to the HPLC enantioseparation of various chiral compounds. The perphenylcarbamatedCDCSP (CCP-CSP) exhibited excellent chiral recognition of a wide range of analytes including racemic aryl alcohols, flavonoids, bendroflumethiazide, atropine and some -blockers. Methanol proved to be a better organic modifier than acetonitrile for most of the analytes with the exception of bendroflumethiazide. The "click" chemistry immobilized permethylated CD CSP (CCM-CSP) afforded poor chiral recognition for most analytes, but could resolve non-aromatic ionone derivatives which were not separated on CCP-CSP. These results suggest that resolution with cyclodextrin derived CSPs depend on a complex interplay of 'host'-'guest' inclusion, hydrogen bonding, - and hydrophobic interactions.