Chiral ligand exchange membranes were synthesized for potential use in racemic filtration applicable to the pharmaceutical industry. Regenerated cellulose membranes with 1 kDa molecular weight cutoff (MWCO) were grafted with chiral L-proline-copper complexes through an intermediate epoxy-silane surface functionalization reaction performed for various times (0, 1.5, 3, 6, 12 and 24 h). The resulting membranes were evaluated in single component diffusion experiments with D or L-Phenylalanine (Phe), which showed much higher permeability for D-Phe compared with L-Phe. The membranes were then evaluated under pressure-driven, single enantiomer filtration and all grafted membranes exhibited predicted enantiomeric excess, with the 6 h epoxy-silane modified membrane yielding 100% enantiomeric excess (EE) over the largest throughput. An equimolar racemic mixture of D, L-Phe was subsequently used to challenge the optimum 6 h epoxy-silane modified membrane, and a two-tiered breakthrough curve was obtained. As predicted by the single enantiomer filtration results, the membrane was shown to completely fractionate the enantiomers at Peclet numbers of similar to 400. The high Peclet number during filtration combined with complete enantiomer fractionation is very intriguing as a competitive technology to chiral chromatography. Simply exposing the membrane surface to the epoxy-silane, L-proline, and copper solution presents a facile and scalable method for membrane surface modification.