The invention provides an online monitoring device, monitoring method and system for lubricating oil of a gearbox of a wind turbine generator. The device comprises a lubricating oil monitoring bypass, an online monitoring device, a data transmission and control module, a cloud server and a client. The lubricating oil monitoring bypass is connected to a main oil way of a gearbox outlet in parallel, lubricating oil is led out from the main oil way, when the lubricating oil flows through the online monitoring device, real-time data of various parameters of oil liquid are comprehensively collected and sent to the data transmission and control module, then the data are uploaded to the cloud server through wireless communication setting on the module, after the client obtains the monitoring data, the monitoring data are comprehensively processed and analyzed through a system software program according to compensation parameters obtained through an early-stage experiment, effective monitoring of the quality of the lubricating oil is achieved, a certain basis is provided for follow-up control measures and fault diagnosis, and basic maintenance, regulation and control operation is achieved through the data transmission and control module. According to the device, the method and the system, the requirement of off-line detection is met, and the defect of off-line detection is overcome.