The CH/pi contact structures of the fucose phenol and fucose indole complexes and the stabilization energies by formation of the complexes (E(form)) were studied by ab initio molecular orbital calculations. The three types of interactions (CH/pi and OH/pi interactions and OH/O hydrogen bonds) were compared and evaluated in a single molecular system and at the same level of theory. The E(form) calculated for the most stable CH/pi contact structure of the fucose phenol complex at the CCSD(T) level (-4.9 kcal/mol) is close to that for the most stable CH/pi contact structure of the fucose benzene complex (-4.5 kcal/mol). On the other hand the most stable CH/pi contact structure of the fucose indole complex has substantially larger E(form) (-6.5 kcal/mol). The dispersion interaction is the major source of the attraction in the CH/pi contact structures of the fucose phenol and fucose indole complexes as in the case of the fucose benzene complex. The electrostatic interactions in the CH/pi contact structures are small (less than 1.5 kcal/mol). The nature of the interactions between the nonpolar surface of the carbohydrate and aromatic rings is completely different from that of the conventional hydrogen bonds where the electrostatic interaction is the major source of the attraction. The distributed multipole analysis and DFT-SATP analysis show that the dispersion interactions in the CH/pi contact structure of fucose indole complex are substantially larger than those in the CH/pi contact structures of fucose benzene and fucose phenol complexes. The large dispersion interactions are responsible for the large E(form) for the fucose indole complex.