A machine status and user behavior analysis system includes a detection side device and an analysis side device. The detection side device is electrically connected with the machine. The detection side device includes a data retrieving module, a sensing module, and a data processing module. The data retrieving module retrieves internal data of the machine. The sensing module senses the status of the machine to obtain sensed data. The data processing module processes the internal data of the machine and the sensed data to classify the internal data of the machine and the sensed data into machine status data and operation condition data. The analysis side device is wirelessly connected with the detection side device to receive the machine status data and the operation condition data. The analysis side device includes a data recognizing module which recognizes the machine status data to find a machine abnormal status and recognizes the operation condition data to find user behavior.