The competitive conformation chirality of dynamically racemic water-soluble pillar[5]arene WP5 can be induced by 19 different l-amino acid ethyl ester hydrochlorides. Among them, l-Arg-OEt and 18 other l-amino acid ethyl ester hydrochlorides can induce the opposite-handedness conformation of WP5. This was ascribed to the different binding models with a side-chain moiety or ethyl ester moiety of amino acids toward the cavity of WP5.