The importance of size and charge of carbohydrate moiety in tofu whey–carbohydrate conjugates, formed through Maillard-type glycosylation, was investigated. Tofu whey (TW) ultrafiltered fractions (UFTW > 3 kDa and UFTW < 3 kDa), acid-precipitated protein (APP), β-conglycinin (7S) or glycinin (11S) were covalently conjugated with carbohydrates (galactomannan (GM), okara polysaccharides, xyloglucan (XG), chitin and chitosan oligo), through naturally-occurring Maillard-type glycosylation at controlled temperature (60 °C), relative humidity (65%) and pH (7.0) for 7-days. The UFTW > 3 kDa fraction conjugated to polysaccharides or oligosaccharides showed improved emulsifying activity index (EAI) and emulsion stability (ES) ( p < 0.05). The UFTW < 3 kDa, APP, 11S and 7S–oligosaccharide conjugates showed almost 3.0 times improvement in ES but no significant difference in EAI. In addition, UFTW < 3 kDa, APP, 7S, and 11S–chitosan oligo conjugates showed 5.0 times lower EAI and ES than those conjugates with XG or chitin oligo, due to electrostatic interaction between the negatively-charged groups of soy protein and positively-charged groups of chitosan oligo. Tofu whey fraction–carbohydrate glycoproteins showed both high and low water or oil-binding capacities, implying that different carbohydrates utilised in the preparation of glycoproteins possess different properties and mechanism in water or oil-binding capacity.