Previous studies have shown chitosans (50–190 kDa) reduce the formation of acrylamide in the Maillard reaction model system. Low-molecular-weight chitosans (52.5 kDa, 71.4 kDa, and 189 kDa) and chitooligosaccharide (1.2 kDa) were added to model systems of glucose/fructose-asparagine solutions in order to evaluate the impact of these substances on the Maillard reaction. The addition of any of chitosans and chitooligosaccharide resulted in a formation of 5-hydroxymethyl furfural (HMF), but acrylamide formation decreased with decreasing molecular weight of the added substances. The amount of acrylamide measured was 17–20 times more than the HMF concentration in each test solution, but no HMF product was detected in the glucose/fructose-asparagine controls. The addition of chitooligosaccharide to either model system can reduce the pH of the solution after heating. HMF is prone to form at acidic pH, as well as lower pH inhibits the Maillard reaction and the formation of acrylamide. The addition of chitooligosaccharide was found to be a viable approach for the mitigation of acrylamide in food preparation.