This report describes a novel approach to direct chiral separations using bare silica stationary phase with an aqueous mobile phase containing sodium phosphate, ß-cyclodextrin (ß-CD), and 2-methyl-2-propanol. Two racemic cycloheptaindole derivatives were used as model compounds for the study. Both enantiomer pairs were resolved in a single chromatographic run. Analyte retention mechanisms were consistent with ion-exchange, ß-CD inclusion, and hydrophobic modes of interaction. Adding triethylamine to the mobile phase improved peak symmetry and reduced retention. Consistent separations were obtained with different lots of ß-CD and different analytical columns. The technique has a number of attractive features that may broaden the use of chiral mobile phase additives for direct enantioseparations.