Thermal processing and Maillard reaction (MR) affect the nutritional and sensorial qualities of milk. In this paper an olive mill wastewater phenolic powder (OMW) was tested as a functional ingredient for inhibiting MR development in ultrahigh-temperature (UHT)-treated milk. OMW was added to milk at 0.1 and 0.05% w/v before UHT treatment, and the concentration of MR products was monitored to verify the effect of OMW phenols in controlling the MR. Results revealed that OMW is able to trap the reactive carbonyl species such as hydroxycarbonyls and dicarbonyls, which in turn led to the increase of Maillard-derived off-flavor development. The effect of OMW on the formation of Amadori products and N-ε-(carboxymethyl)-lysine (CML) showed that oxidative cleavage, C2–C6 cyclization, and the consequent reactive carbonyl species formation were also inhibited by OMW. Data indicated that OMW is a functional ingredient able to control the MR and to improve the nutritional and sensorial attributes of milk.