The two best aromatic-functionalized cyclofructan chiral stationary phases, R-naphthylethyl-carbamate cyclofructan 6 (RN-CF6) and dimethylphenyl-carbamate cyclofructan 7 (DMP-CF7), were synthesized and evaluated by injecting various classes of chiral analytes. They provided enantioselectivity toward a broad range of compounds, including chiral acids, amines, metal complexes, and neutral compounds. It is interesting that they exhibited complementary selectivities and the combination of two columns provided enantiomeric separations for 43% of the test analytes. These extensive chromatographic results provided useful information about method development of specific analytes, and also gave some insight as to the enantioseparation mechanism.