Lactose-hydrolyzed (LH) ultrahigh temperature (UHT) processed milk is more prone to Maillard reactions and formation of advanced glycation end products (AGEs) during processing and storage than conventional (CON) UHT milk because of the presence of free galactose and glucose. Commercially available β-d-galactosidases with transgalactosylating activity can incorporate galactose into galactooligosaccharides (GOSs) and potentially limit Maillard reactions in this lactose-reduced GOS-containing milk. The aim of this study was to examine the extent of Maillard reactions in a lactose-reduced GOS milk compared to LH and CON milk after UHT processing. The GOS milk had significant lower levels of lysine- and arginine-derived AGEs compared to LH milk, while their concentrations were similar to those found in CON milk. The total concentration of measured Arg-derived AGEs was similar to the total concentration of Lys-derived AGEs in the three types of milk, indicating that Arg is an important source of AGEs in milks. Interestingly, the GOS milk generated threefold higher concentrations (up to 330 ± 6 μM) of 3-deoxyglucosone (3-DG, a C6 α-dicarbonyl). These results demonstrate that GOS milk could be a potential alternative for LH milk for lactose-intolerant individuals, although further studies are needed to understand the increased formation of 3-DG in GOS-containing milk.