Triboelectric nanogenerators (TENGs) have potential to achieve energy harvesting and condition monitoring of oils, the “lifeblood” of industry. However, oil absorption on the solid surfaces is a great challenge for oil–solid TENG (O-TENG). Here, oleophobic/superamphiphobic O-TENGs are achieved via engineering of solid surface wetting properties. The designed O-TENG can generate an excellent electricity (with a charge density of 9.1 µC m⁻² and a power density of 1.23 mW m⁻²), which is an order of magnitude higher than other O-TENGs made from polytetrafluoroethylene and polyimide. It also has a significant durability (30,000 cycles) and can power a digital thermometer for self-powered sensor applications. Further, a superhigh-sensitivity O-TENG monitoring system is successfully developed for real-time detecting particle/water contaminants in oils. The O-TENG can detect particle contaminants at least down to 0.01 wt% and water contaminants down to 100 ppm, which are much better than previous online monitoring methods (particle > 0.1 wt%; water > 1000 ppm). More interesting, the developed O-TENG can also distinguish water from other contaminants, which means the developed O-TENG has a highly water-selective performance. This work provides an ideal strategy for enhancing the output and durability of TENGs for oil–solid contact and opens new intelligent pathways for oil–solid energy harvesting and oil condition monitoring.