Modern industrial applications involve rigorous operating conditions due to which lubricant either slips out of the contact or its thin layer resides between the interacting surfaces. Deposition of diamond-like carbon coatings and using lubricants capable of physically adsorbing on the interacting surfaces can significantly improve tribological performance. In this study, tribological compatibility of glycerol mono-oleate, molybdenum dithiocarbamate and zinc dialkyldithiophosphate with palm trimethylolpropane ester and tetrahedral amorphous diamond-like carbon coating has been investigated using universal wear testing machine. For comparison, additive-free and formulated versions of polyalphaolefin were used. Moreover, spectroscopic techniques were used to investigate mechanisms responsible for a particular tribological behavior. Among base oils, trimethylolpropane ester proved to be more effective in enhancing friction performance and mitigating wear of contacts when one of the interacting surfaces was ferrous-based. Self-mated tetrahedral amorphous diamond-like carbon coating surfaces resulted in lowest values of friction and wear coefficient of balls.