Separation of the enantiomers of each of three different racemates, neutral rac -α-tetralol, acidic rac -2-phenylpropionic acid, and basic rac -1-phenylethylamine, using subcritical and supercritical fluid chromatography with two different chiral stationary phases, heptakis(2,3,6- tri - O -methyl)-β-cyclodextrin (Sumichiral OA-7500 column) and tris(3,5-dimethylphenylcarbamate) of amylose (Chiralpak AD-H column), was compared. The elution order of the enantiomers of the three racemates was determined, and the effects of the type of alcohol modifier, column oven temperature, mobile phase composition, flow rate, and pressure were examined. The most appropriate column oven temperature depended on both the type of alcohol modifier and the compound analyzed. Lower alcohol content improved the peak separation of both rac -α-tetralol on the Sumichiral OA-7500 column and rac -1-phenylethylamine on the Chiralpak AD-H column, while the same phenomenon was not observed with either rac -α-tetralol or rac -2-phenylpropionic acid on the Chiralpak AD-H column. Decreasing outlet pressure improved the peak separation obtained with rac -2-phenylpropionic acid, but had little effect on either rac -α-tetralol or rac -1-phenylethylamine.