This paper deals with studies on the optical resolution of glycyl-DL-amino acid dipeptides and diastereomeric dipeptides on three different chemically bonded chiral ligand exchange chromatography (LEC)-phases. The phases were prepared by binding L-proline or L-hydroxyproline to silica gel using different silanes as spacer. Using 10−5M copper(H) sulface as a mobile phase, eleven glycyl-dipeptides were resolved, nearly all of them with baseline separations. Several dipeptides containing two stereogenic centres were at least partially resolved into the four stereoisomers.