Maillard Reaction (MR) was performed in ‘dry’ conditions at 50 °C for 48 h between native shrimp hydrolysate (HN) and xylose or dextran. Resulting emulsifying and antioxidant properties were assessed. HN was compared with a native sodium caseinate (CN) and its glycoconjugates, obtained in the same conditions. Compared to dextran, xylose resulted in significant browning after MR with HN or CN, but HN-xylose conjugates showed the most functional modifications. Increasing xylose/HN ratios led to significant molecular rearrangements in the peptide populations and intermediate aromatic compounds of the MR detected at 220 and 294 nm, respectively. Consequently, HN-xylose conjugates had higher reducing power than HN. Conversely, at 0.5% (w/w), a sharp increase in consistency index and apparent viscosity of emulsions after a 4-h ageing period was obtained with the lowest xylose/HN ratio. These results confirm that MR is a promising process for the production of new natural food ingredients from marine-derived protein sources.