Crystals of the title complex, C(3)H(7)NO(2).C(8)H(8)O(3).0.5H(2)O, were obtained from an aqueous solution containing racemic mandelic acid and (S)-alanine. The unit cell includes two independent molecular complexes and one water molecule. The structure formed by (R)-mandelic acid and (S)-alanine in a 1:1 molar ratio shows the successful optical separation of racemic mandelic acid. Strong hydrogen bonding, with a rather short O...O separation of 2.494 (3) A, is observed between the carboxyl and carboxylate groups. A structural comparison suggests that the strong hydrogen bonding affects the neighbouring covalent bond.