In this study, chitooligosaccharide (COS) and glycine (Gly) were selected to prepare Maillard reaction products, which were designated COS-Gly-MRPs. Changes in the FTIR and fluorescence spectra confirmed the formation of the COS-Gly-MRPs. Using ferric reducing antioxidant power (FRAP) as a response, the optimal reaction conditions, i.e., a time of 107 min, temperature of 121 °C, pH of 6.0, and : = 2.5:1, were obtained by one-variable-at-a-time method and by response surface methodology. The resulting COS-Gly-MRPs exhibited much stronger antioxidant activity than their substrates. The FRAP of COS-Gly-MRPs was 32.14 mmol Fe/L, and the radical scavenging activity of COS-Gly-MRPs reached 78.6, 89.0, 92.3, and 86.0% for ABTS, superoxide, DPPH, and hydroxyl radicals, respectively. After 7 days of storage, COS-Gly-MRPs-treated fruit juices showed higher antioxidant capacity than those treated with a mixture of COS and Gly.