Two kinds of molecules, one recognizing the sialo-/asialo-N-acetyllactosamine structures and the other recognizing the Lewis X structure in a divalent cation-independent manner, were detected on the head of boar sperm prepared from cauda epididymis by fluorescence-labeled or biotinylated dextran-based multivalent oligosaccharide probes. The N-acetyllactosamine recognition molecule(s) is weakly detected on uncapacitated sperm and becomes strongly detectable on capacitated sperm. On the other hand, the Lewis X recognition molecule is detected at a moderate level before capacitation and at a high level after capacitation. Both molecules disappear from the sperm head after induction of acrosome reaction and also by mild detergent treatment. Thus, the two kinds of carbohydrate molecules are expressed on the plasma membrane of boar sperm depending on their physiological state. Inhibition study of the oligosaccharide-dextran probe binding to isolated sperm plasma membrane by various glycoproteins, oligosaccharides, and sulfated polysaccharides also supported the occurrence of the two distinct kinds of molecules.