Self-organization mechanisms of metastable dissipative structures during friction depending on base and oil functional additives for hypoid gears are considered. Research was conducted on a software-hardware complex with simulation of gears’ operation in rolling with slipping conditions in start-stop mode. Indicators of formation of wear-resistant dissipative structures include the following: improvement of antifriction characteristics, lubricant boundary layers’ formation, contact surfaces’ strengthening, and formation of heterogeneous deformation microrelief with a fine-grained structure. The formation of chemically modified boundary layers on 90% of the contact area of tribo-coupling elements ensures an increase in the wear resistance of leading and lagging surfaces by 2 and 1.4 times, respectively. The sclerometry method was used to establish that the formation of dissipative structures when lubricating tribo-coupling elements with various transmission oils can reduce deformation processes in metal near-surface layers by 23%. Highly viscous flavored lubricant with distillate oil and additive composition ensures wear-resistant dissipative structures with active components, including oxygen, sulfur, and phosphorus.