The invention provides a monitoring and controlling system of an intelligent lubricating device. The monitoring and controlling system of the intelligent lubricating device comprises a lubricating oilcontaining box which can be compressed in the vertical direction, the upper end surface of the lubricating oil containing box is a plane, and the lower end of the lubricating oil containing box is provided with a first cone oil outlet; an oil outlet cylinder arranged under the lubricating oil containing box, the center of the oil outlet cylinder is vertically provided with a first elastic cylinder, and an oil outlet hole passage is formed in the cylinder; an outer cover is arranged above the lubricating oil containing box in a covering mode; and a controller, wherein a lubricating oil extrusion assembly, located above the lubricating oil containing box, is arranged inside the outer cover; a plurality of annular clapboards used for limiting multiple annular sealed chambers is horizontallyarranged in the oil outlet cylinder, an annular air bell is fixed to the outer wall of the oil outlet cylinder in the circumferential direction, and the annular air bell is connected to an air-suctionand air-inflation dual-purpose pump by an air tube; and the controller is connected with a straight line driver and the air-suction and air-inflation dual-purpose pump. According to the monitoring and controlling system of the intelligent lubricating device, lubricating oil is monitored in real time, manual operation is not required, and timing and quantitative oil injection can be achieved.