Frictional power losses of high-speed and heavy-load herringbone gearboxes increase the temperature of the gearbox. Thus, real-time surface temperature measurement is significant for evaluating the gearbox lubrication design. A rotating gear test rig with an infrared pyrometer is developed in this paper to conduct real-time and accurate temperature measurements of the transverse plane of the oil-jet-lubrication herringbone gear. First, the influencing factors and measuring errors of surface temperature are analyzed using the infrared pyrometer. The emissivity of the measured surface of a gear tooth painted with matte black is experimentally calibrated. Second, the temperature measurement tests of the oil-jet-lubrication herringbone gear under different conditions are carried out. Measurement errors resulting from purge air pressure, purge air temperature, and oil-jet temperature are also experimentally studied. The results indicate that the purge gas flow can reduce the measurement errors of the infrared pyrometer resulting from oil mist with an appropriate purge air pressure and purge air temperature. Finally, a mathematical curve-fitting of the measurement results between the infrared pyrometer and thermocouple is carried out. The calculated temperatures by the curve-fitting formula are compared with the measured thermocouple temperature, with the relative differences being less than 1 °C. Thus, the curve-fitting formula is credible for the real-time measurement of surface temperature, while the relevant measuring method is also valuable for engineering applications of high-speed gear systems under oil-jet-lubrication conditions.