Enantiodifferentiating photoisomerization of (Z)-cyclooctene included and sensitized by m-methoxybenzoyl-beta-cyclodextrin gave chiral (E)-isomers in up to 46% enantiomeric excess, which is the highest value ever reported for supramolecular photochirogenesis with analogous hosts, thus demonstrating the crucial role of the sensitizer-spacer moiety in supramolecular photochirogenic systems.