Two N-containing borates, BTES and BMES, were synthesized with dodecyl phenol, 2-(N-containing heterocyclic) ethan-1-ol, boric acid, and dibutylamine, and their tribological properties in rapeseed oil (RSO) were investigated using a four-ball tester. The results showed that the load-carrying ability ( P B value) of RSO can be improved by 40.9% and 67.9%, respectively, when using 0.5 wt% BTES and BMES. Moreover, the antiwear and friction-reducing performances of the additive-containing oils increased with the additive concentration. The X-ray photoelectron spectroscopy results of the worn steel ball surfaces showed that BTES and BMES formed protective films, which contained boron oxide, iron oxide, ferrous sulfate, ferrous sulfide (for BMES), and other organic nitrogen compounds, on the metal surfaces. The better load-carrying and antiwear performances of BMES than those of BTES might be due to their different sulfur contents, which result in different tribochemical reaction films on the contact surfaces. The oxidation stability tests showed that BTES and BMES possessed synergistic antioxidation activity with N-phenyl-α-naphthylamine (T531), and consequently, the oxidation activation energy of the oil sample increased by 77.85% and 82.19%, respectively, compared with that of RSO when the oil sample contained 0.05 wt% BTES/BMES and 0.25% T531.