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Abstract: A tailor-made catalyst design was attempted for a required substrate specificity by the authors' footprint imprinting method. Two silica(alumina) footprint catalysts were prepared by imprinting with N-benzoylbenzenesulfonamide (1) and N-(p-toluoyl)-p-toluenesulfonamide (2) from the same aluminum ion-doped silica gel. Their catalytic effects upon 2,4-dinitrophenolysis of benzoic anhydride, p-, m-, and o-toluic anhydrides were compared in order to find any difference in substrate specificities. The catalyst prepared by imprinting with 1 showed the largest specificity(kcat/Km) toward benzoic anhydride, whereas the catalyst prepared with 2 showed the largest specificity toward p-toluic anhydride. This finding evidently demonstrated that the substrate specificities of footprint catalytic sites are alterable, as required through selecting appropriate transition state analogs as template molecules for footprint marking.